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マスタードガス

Sulfur Mustard

HCID 10461
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
505-60-2
標準SMILES
ClCCSCCCl
InChIKey
QKSKPIVNLNLAAV-UHFFFAOYSA-N
分子式
C4H8Cl2S
平均分子量
159.08 g/mol
単同位体質量
157.9723768

概要

Sulfur mustard (HD) is a thick liquid at ambient temperature, but becomes a solid at 58 °F. It is heavier than water as a liquid and heavier than air as a vapor. It does not occur naturally in the environment It is often called mustard gas, but sulfur mustard is not likely to change into a gas immediately if it is released at ordinary temperatures. As a pure liquid, it is colorless and odorless, but when mixed with other chemicals, it looks brown and has a garlic-like smell. Sulfur mustard has been used in chemical warfare and was made in large amounts during World Wars I and II. It was reportedly used in the Iran-Iraq war in 1980-1988. It is not presently used in the United States, except for research purposes, and the U.S. Department of Defense must destroy all remaining stocks of sulfur mustard by 2004.

名称と識別子

優先名称
Sulfur Mustard
IUPAC
1-chloro-2-(2-chloroethylsulfanyl)ethane
現地名
マスタードガス
英語名
Mustard gas
分子式
C4H8Cl2S
分子量
159.08

名称と別名

Mustard gasSulfur mustardYperiteSenfgasIpritLostBis(2-chloroethyl) sulfide505-60-2Schwefel-lostYellow cross liquidMustard, sulfurDistilled mustard
名称をさらに表示
スルファマスタード化学兵器ロスト2,2'-チオビス(1-クロロエタン)1,5-ジクロロ-3-チアペンタンS-ロストS-マスタード1-クロロ-2-(2-クロロエチルチオ)エタンビス(2-クロロエチル)スルフィドイペリットイプリット2-クロロエチル(2-クロロエチル)スルフィドβ,β'-ジクロロジエチルスルフィド硫化ビス(2-クロロエチル)ロスト硫黄マスタード薬剤HD1,1'-チオビス(2-クロロエタン)ビス(2クロロエチル)スルフィド硫黄マスタード類硫黄マスタード類、SULFURMUSTARDSULPHURMUSTARDDichlorodiethyl sulfidebis-β-chloroethyl sulfideBIS(2-CHLORETHYL)SULPHIDEβ,β'-dichloroethyl sulfideBIS(2-CHLOROETHYL)SULPHIDE

物性

構造計算による物性

XLogP
2.1
極性表面積
25.3 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
4
重原子数
7
形式電荷
0
複雑度
28.9

実験および物理化学的性質

Chemical Classes · 3 件

Toxic Gases & Vapors -> Chemical Weapons

Carcinogens

-> NIOSH Emergency Response Categories

SpringerMaterials PropertiesBoiling point
LogP · 2 件

log Kow = 2.14 /Estimated by EVA (Experimental Value Adjusted) method using measured value of bis(2-chloroethyl) ether (1.29)/

1.37/2.41

Odor · 2 件

Weak, sweet, agreeable odor

Garlic-like odor

Density · 5 件

1.274 at 68 °F (EPA, 1998) - Denser than water; will sink

1.2741 at 20 °C/4 °C (liquid); 1.338 at 13 °C (solid)

Relative density (water = 1): 1.27

1.274

1.27 @ 20°C

Viscosity3.95 cS at 20 °C
Color/Form · 4 件

Colorless, oily liquid when pure

Yellow prisms

Oily liquid ... forms prisms on cooling

Water clear if pure. Normally pale yellow to black

Solubility · 6 件

In water, 609 mg/L at 25 °C

In water, 684 mg/L at 25 °C

In water, 920 mg/L at 22 °C

Soluble in fat solvents and other common organic solvents; high lipid solubility

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

危険有害性情報

Regulatory Information · 2 件

Hazard Traits - Carcinogenicity

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety Information- Indoor Air: Sulfur mustard can be released into indoor air as a liquid spray (aerosol) or as a vapor.
DOT LabelPoison
Fire Hazards · 2 件

For information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Combustible under specific conditions.

Fire Potential · 2 件

Combustible when exposed to heat or flame: can be ignited by a large explosive charge.

Material itself does not burn or burns with difficulty.

Health HazardsFor information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
Hazards Summary · 3 件

化学と産業

薬理情報

Mechanism of Action · 5 件

Low-dose exposure of alkylating mustard gas causes long-term respiratory complications characterized by bronchitis and lung fibrosis. In this study, we utilized a mouse model for lung exposure of the nitrogen mustard melphalan, in order to define early and late events in the pathogenesis such as expression of pro-inflammatory cytokines, recruitment of inflammatory cells to airways and late-phase fibrosis. /The authors/ investigated the roles of different T lymphocyte subsets on the inflammatory response by using knockout mice lacking either the genes expressing T cell receptor (TCR)-alpha beta or TCR-gamma delta, and compared the responsiveness with that of wild type mice and double knockout mice completely deficient in T cells. Exposure to melphalan induced an early burst of the pro-inflammatory cytokines interleukin (IL)-1beta, IL-6 and IL-23 in airways, followed by extensive infiltration of neutrophils in the lung tissue and airways within 24hr. The acute phase was followed by a sustained lymphocytic response that persisted for at least 14 days with resulting lung fibrosis. Engagement of T lymphocytes, particularly the gamma delta T cell subset, was crucial both for the acute cytokine and neutrophil response and for the late-phase lung fibrosis as indicated by the lack of response in gamma delta T cell deficient mice. /The/ data demonstrate that T lymphocytes play a prominent role in the pathogenesis of long-term lung injuries caused by strong alkylating agents.

Sulphur mustard (SM) is a chemical warfare agent that causes erythema and blistering of the skin with a latency of several hours. Although SM is known for almost 200 years the cellular mechanisms involved in the damaging process are not fully understood. There is evidence that changes in nitric oxide (*NO), reactive oxygen species (ROS) and reactive nitrogen species (RNS) might be involved in the damaging process.To find out more about the pathophysiology of SM, /the authors/ investigated the initial formation of biochemical markers of nitrosative and oxidative stress as well as activation (translocation from plasma-membrane) and upregulation of eNOS and iNOS, respectively. Human immortalized keratinocytes (HaCaT cell line) were exposed to SM (100 uM or 300 uM) for 30 min. Cells were fixed after 1hr, 3hr or 6hr of incubation in SM-free medium and immunostained. Live cell experiments were performed using the NO-sensitive dye DAF2-DA. In order to assess cell viability after BH(4) supplementation, /investigators/ analyzed apoptosis using CDD-ELISA. SM significantly increased biochemical markers of nitrosative and oxidative stress already 1hr after exposure. Moreover, the NO producing enzymes eNOS and iNOS showed concentration- and time-dependent changes in their activation or expression levels. Initially, live cell imaging experiments could not confirm NO production after SM exposure. Only when cells were supplemented with tetrahydrobiopterine, stable NO production was detectable. Apoptotic activity was increased due to SM exposure and could be reduced after BH(4) treatment. Our data point towards concentration- and time-dependent formation of iNOS and activation of eNOS due to translocation from plasma-membrane. Live cell experiments yielded first indications of catalytic decoupling of NOS that could be reversed by supplementation with tetrahydrobiopterin (BH(4)). Addition of BH(4) 1hr after SM exposure significantly decreased apoptosis compared to the unsupplemented control.

関連反応

2 件
反応記録を作成
HRID 1085127 の反応式
HRID 1085127反応物としてuspto-grants-1991_04
HRID 1480985 の反応式
HRID 1480985反応物としてuspto-grants-2016_08

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
QKSKPIVNLNLAAV-UHFFFAOYSA-N
S-LostGelbkreuzKampstoff lostMustard vaporS-yperiteAgent hdS MustardYellow cross gas

データベース識別子

CAS
505-60-2
PubChem CID
10461
DTXSID
DTXSID0037100
ChEMBL
CHEMBL455341
ChEBI
CHEBI:25434
UNII
T8KEC9FH9P
EC Number
684-527-7
Nikkaji
J1.571G

For more Solubility (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (7 total), please visit the HSDB record page.

Solubility in water, g/100ml at 25 °C: 0.0068 (very poor)

CorrosivityRapidly corrosive to brass at 65 °C; will corrode steel at a rate of .0001 in. of steel per month at 65 °C
Flash Point · 4 件

221 °F (EPA, 1998)

104 °C

105 °C

221 °F

Boiling Point · 4 件

419 to 423 °F at 760 mmHg (EPA, 1998)

215-217 °C at 760 mm Hg

216 °C

419-423 °F

Decomposition · 2 件

In pure aqueous media, most sulfur mustard is hydrolyzed to thiodiglycol and hydrochloric acid.

When heated to decomposition ... emits highly toxic fumes of /sulfur oxides and hydrogen chloride/.

物理化学的性質

融点
13 · 13-14°
沸点
760 · bp760 215-217°; bp10 98°
比重(密度)
13 · d13 1.338 (solid); d420 1.2741 (liq)
蒸気密度
5.4 · 5.4
屈折率
20 · nD20 1.53125
闪点
221 °F · 221°F
外見
液体
色
無色(純粋の場合)~淡黄色の油状液体
水溶解度
0.69 g/L · 0.69g/L(25℃)
Henry's Law Constant
3 · 3.0×10-1 mol/(m3Pa) at 25℃, Hine and Mookerjee (1975)
EPAの化学物質情報
Mustard gas (505-60-2)

化学的性質

化学的特性Mustard gas, a chlorinated sulfur compound(s), is an oily, yellow to black liquid (clear when pure). It has a sweet, burnt garlic or horseradish-like odor. The odor threshold for HD is 0.0006 milligram per cubic meter.

Sulfur mustard (HD) is a thick liquid at ambient temperature, but becomes a solid at 58 °F. It is heavier than water as a liquid and heavier than air as a vapor. It does not occur naturally in the environment It is often called mustard gas, but sulfur mustard is not likely to change into a gas immediately if it is released at ordinary temperatures. As a pure liquid, it is colorless and odorless, but when mixed with other chemicals, it looks brown and has a garlic-like smell. Sulfur mustard has been used in chemical warfare and was made in large amounts during World Wars I and II. It was reportedly used in the Iran-Iraq war in 1980-1988. It is not presently used in the United States, except for research purposes, and the U.S. Department of Defense must destroy all remaining stocks of sulfur mustard by 2004.

After inhalation, it has delayed effects 2-24 hours after exposure. It penetrates the skin in 1-2 minutes without initial irritation. It is corrosive to skin and lung tissue resulting in skin blisters and hemoptysis. [NIOSH Emergency Response Card] A lethal dose is about 1.5 tsp. or enough to cover about 25% of the body surface area. Mustard is an alkylating agent that disrupts cell function by reacting with DNA and other macromolecules. The eyes, skin, and respiratory tract are most commonly affected by mustard poisoning. High doses also damage the hematopoietic, gastrointestinal, and central nervous systems. Death is usually caused by pulmonary injury, immunosuppression, and secondary infections. Most casualties recover completely after treatment of first and second degree burns. Victims who have lost vision should be reassured that it is temporary. [ccc.apgea.army.mil] Causes lachrymation; [ICSC] Thiodiglycol can be detected in the urine for about one week. Initial leukocytosis may be followed in 3-5 days by bone marrow depression. Chest x-ray may show evidence of chemical pneumonitis within a few days. [Weinstein, p. 136] 2,2'-dichlorodiethylsulfide (mustard gas) is classified by IARC as a human carcinogen, and it has a MAK skin designation. Mustard gas is fibrogenic to the lungs in the context of an acute inhalation exposure complicated by bronchiolitis obliterans.

The major hazards encountered in the use and handling of bis(2-chloroethyl)sulfide stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, or dermal contact), exposure to this sweet-smelling, colorless, oily liquid may occur from its storage, transport, or use in organic synthesis. Effects from exposure occur from its severe irritant properties and may include blistering/necrosis of the skin, corneal ulceration/blindness, and pulmonary edema, all of which may be delayed in onset. Bis(2-chloroethyl)sulfide has been indicated as a human carcinogen (Group 1) by the International Agency for Research on Cancer (IARC). Exposure should be controlled by mechanical ventilation. In activities and situations where over-exposure may occur, wear appropriate chemical protective clothing and a positive pressure, self-contained breathing apparatus. If exposure should occur, immediately flush contaminated skin or eyes with water and neutralize with a 2.5 per cent solution of sodium thiosulfate. Contaminated clothing should be removed and discarded or left at the work site for cleaning before reuse. Smoking, eating, and drinking should be prohibited in bis(2-chloroethyl)sulfide, prolonged exposure to fire or heat may cause cylinders to violently rupture and rocket. For fires involving this substance, extinguish with dry chemical, CO2, foam, or water. Fight fire from as far a distance as possible. Bis(2-chloroethyl)sulfide should be stored in dry areas, away from heat, sources of ignition, and strong oxidizers. Spills of this substance should be prohibited from entering water sources and sewers. Before implementing land disposal of bis(2-chloroethyl)sulfide waste, consult with environmental regulatory agencies for guidance.

Reactive GroupHalogenated Organic Compounds
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
Explosion Hazards- When heated, vapors may form explosive mixtures with air, presenting an explosion hazard indoors, outdoors, and in sewers.
Special Reports · 5 件

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Mustard gas (505-60-2) is known to be a human carcinogens. First listed in the First Annual Report on Carcinogens (1980).[Available from, as of August 10, 2013: http://ntp.niehs.nih.gov/]

Gupta RC, ed. Handbook of Toxicology of Chemical Warfare Agents. Amsterdam: Academic Press (2009). This handbook provides in-depth information on chemical warfare agents and covers every aspect of deadly toxic chemicals used as weapons of mass destruction and employed in conflicts, warfare and terrorism.

IPCS; Poisons Information Monograph 354. Mustard Gas. (September 1996).[Available from, as of July 10, 2007: http://www.inchem.org/documents/pims/chemical/mustardg.htm]

Pechura CM and Rall DP, Eds; Committee to Survey the Health Effects of Mustard Gas and Lewisite, Institute of Medicine, National Academies of Science; Veterans at Risk: The Health Effects of Mustard Gas and Lewisite. National Academy Press, Washington, DC (1993). The primary task of this study was a survey of the scientific and medical literature on the health effects of mustard gas and Lewisite published from 1917 to 1993. This information, along with information supplied by interested parties at presentations to the Committee, were used to assess possible risks to the 60,000 soldier volunteers who were exposed to Lewisite and sulfur mustard in human experiments conducted during World War II.

For more Special Reports (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (13 total), please visit the HSDB record page.

Reactivity AlertsWater-Reactive

安全と保護具

Fire Fighting · 3 件

For information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

In case of fire in the surroundings, use appropriate extinguishing media.

- Sulfur mustard is combustible.

First Aid Measures · 4 件

Fresh air, rest. Half-upright position. Artificial respiration may be needed. No mouth-to-mouth artificial respiration. Administration of oxygen may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Wear protective gloves when administering first aid. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Do NOT induce vomiting. NO mouth-to-mouth artificial respiration. Administration of oxygen may be needed. Refer for medical attention .

First AidFor information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
Safe StorageSeparated from water and food and feedstuffs. Well closed. Ventilation along the floor. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 1 件

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 3 件

Water, fog, foam, CO2, dry chemical. Avoid methods that cause splashing or spreading. Fight fire from as far a distance as possible.

To fight fire, use water, foam, carbon dioxide, dry chemical

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

Storage Conditions · 1 件

Store in tightly closed containers in a cool, well vented area away from oxidizers. Where possible, automatically pump liquid from drums or other storage containers to process containers. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with ASHO standard 1910.1045.

Cleanup Methods · 2 件

Cover with vermiculite, diatomaceous earth, clay, or fine sand and neutralized as soon as possible using large amounts of 5% sodium hypochlorite solution. Scoop up all material and place in an approved container. After sealing, decontaminate the exterior and label. All leaking containers should be packed with sorbent (e.g. vermiculite) and placed between the interior and exterior containers. Label and dispose according to regulations. Conduct general area monitoring. If sodium hypochlorite solution is not available then use the following in order of preference: Calcium Hypochlorite and Super Tropical Bleach Slurry (STB). WARNING: Pure, undiluted Calcium Hypochlorite (HTH) will burn on contact with liquid blister agent.

To clean up spill, cover up to 15 percent calcium hypochloride. Place in container; neutralize after 12 hours if necessary. Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Attempt to stop leak if hazard. Use water spray to knock down vapors. Avoid breathing vapors and bodily contact with material. Keep upwind. Wash away any material, which may have contacted the body, with copious amounts of soap and water. Downwind evacuation must be considered. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of confined spaces, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build up of explosive concentrations. ...

Nonfire Spill ResponseFor information on chemical warfare blister agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
Disposal Methods · 5 件

Principles and methods for destruction of chemical weapons: ... "Destruction of chemical weapons" means a process by which chemicals are converted in an essentially irreversible way to a form unsuitable for production of chemical weapons, and which in an irreversible manner renders munitions and other devices unusable as such. ... Each /nation/ shall determine how it shall destroy chemical weapons, except that the following processes may not be used: dumping in any body of water, land burial or open-pit burning. It shall destroy chemical weapons only at specifically designated and appropriately designed and equipped facilities. ... Each /nation/ shall ensure that its chemical weapons destruction facilities are constructed and operated in a manner to ensure the destruction of the chemical weapons; and that the destruction process can be verified under the provisions of this Convention. /Chemical warfare agents/

Destruction of U.S. stockpiles of chemical agents, including sulfur mustards, was mandated by the Chemical Weapons Convention to take place before April 2007.

As part of the Chemical Stockpile Disposal Program (CSDP) mandated by Congress, the Army currently uses the "baseline system" for destruction of munitions and bulk agents containing sulfur mustard. The "baseline system" consists of several steps: (1) storage, transportation, and unloading of munitions and containers, (2) disassembly and draining, (3) agent destruction, (4) energetics destruction, (5) metal parts decontamination, and (6) dunnage (i.e., other contaminated materials) disposal. ...

To address growing public concern over incineration, in 1992, Congress directed the Army to evaluate alternative disposal methods that might be significantly safer and more cost effective than the baseline system. Two alternatives were accepted by the Army for further development: (1) stand alone neutralization followed by incineration and (2) neutralization followed by bio-treatment...

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Spillage Disposal · 1 件

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 件

Hot Zone Responders should be trained and appropriately attired before entering the Hot Zone. If the proper personal protective equipment (PPE) is not available, or if the rescuers have not been trained in its use, call for assistance in accordance with local Emergency Operational Guides (EOG)...

... Patients ... must be decontaminated before being allowed to enter the /Emergency Department/. Decontamination can take place inside the hospital only if there is a decontamination facility with negative air pressure and floor drains to contain contamination. Personnel should wear the same level of protection required in the Hot Zone...

Decontamination procedures should be initiated immediately after exposure. Hypochlorite bleaches were the earliest decontaminants used to detoxify mustard. During World War II, both common bleach [NaOCl-] and superchlorinated bleaches [Ca(OCl-)2] were used. More stable N-chloro compounds, such as chloramine, have been used in more modern personal decontamination systems. In the 1950s, a nonaqueous equipment decontamination solution "DS2" (2% NaOH, 70% diethylenetriamine, 28% ethylene glycol monomethyl ether) was developed in which the conjugate base of the glycol ether reacts rapidly with mustard via double elimination. The currently fielded U.S. ARMY M291 skin decontamination kit contains the decontaminant powder XE-555 resin (Amberguard 555) .

The eyes should be washed immediately with as much water as tolerable, for at least 15 minutes, even if no symptoms are present, since it is known that ocular and dermal symptoms are delayed. Of the many fluids studied for eye irrigation, none has proven more effective than tap water ... Contaminated clothing should be removed and the skin, particularly the groin, axillae, and perineal areas, should be decontaminated. Rapid removal from skin is critical, as sulfur mustard penetrates skin within minutes of exposure. Skin decontamination may be accomplished with copious amounts of water, a 0.5% hypochlorite solution, or a skin decontamination kit.

For more Preventive Measures (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (15 total), please visit the HSDB record page.

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 件

Bis(2-chloroethyl) sulfide levels were detected in the urine of 6 out of 12 patients from the Iran-Iraq War (1986) ranging from 1-30 ppb(1). The same authors had previously identified 1 and 1.5 ppb of bis(2-chloroethyl)sulfide in the urine of two other patients from the Iran-Iraq War(2). Concentrations three orders of magnitude greater than the above have been found in fat and fat-rich organs such as the brain and these are thought to act as a reservoir for a very low concentration of bis(2-chloroethyl)sulfide in the urine(1). Urine samples taken from 9 Iranian patients, victims of an alleged attack by chemical warfare agents, contained 4-110 and 15-90 ng/mL of thiodiglycol, a hydrolysis product of bis(2-chloroethyl)sulfide(3). A 1985 autopsy of body tissue and fluids of an Iranian man who had died 7 days after exposure to mustard gas resulted in the following concentrations (tissue - concentration in ppm wet weight): brain 10.7; cerebrospinal fluid 1.9; liver 2.4; kidney 5.6; spleen 1.5; lung 0.8; muscle 3.9; fat 15.1; skin 8.4; skin with subcutaneous fatty tissue 11.8; blood 1.1; urine below detection limit of approximately 0.1 ppm(4).

Interactions · 5 件

Sulfur mustard (SM) has been used as a vesicant chemical warfare agent. To investigate the respiratory damages it causes, /the authors/ studied the effects on guinea pigs of an intratracheal injection of 0.3 mg/kg of SM 5 hr and 14 days after injection. Five hours after SM intoxication, respiratory system resistance and microvascular permeability were increased. These alterations were not prevented by pretreatment with 50 mg/kg sc of capsaicin 2 wk before SM intoxication. Histological studies showed columnar cell shedding all along the tracheal epithelium, bronchoconstriction, and peribronchial edema. Fourteen days after SM intoxication, guinea pigs demonstrated airway hyperreactivity to aerosolized substance P and histamine. Pretreatment with phosphoramidon caused a further increase in airway responsiveness to substance P. Neutral endopeptidase activity in the tracheal epithelium was decreased by twofold in SM-intoxicated guinea pigs. At this stage, the tracheal epithelium was disorganized and atrophic. These results demonstrate that in guinea pigs SM intoxication induces severe lesions to the tracheal epithelium, which might account for the airway hyperresponsiveness observed 14 days after intoxication.

The chemical warfare agents sulfur mustard (SM) and nitrogen mustards (HN-1, HN-2, and HN-3) are highly reactive vesicants. The study was planned to investigate the protective efficacy of amifostine, DRDE-07 and their analogues, and few conventional antidotes (30 minutes pretreatment) against dermally applied SM and nitrogen mustards in preventing hematological and biochemical changes in mice. Mustard agents (1.0 median lethal dose [LD(50)]) induced a significant decrease in the body weight and spleen weight. A significant decrease in the white blood cell (WBC) count and an increase in serum transaminases and alkaline phosphatases (ALPs) were observed. A significant decrease in reduced (GSH) and oxidized glutathione (GSSG) and an increase in thiobarbituric acid reactive substances were also observed. All the mustard agents increased DNA fragmentation. The effects of SM were significantly ameliorated by DRDE-07 analogues, and with nitrogen mustards the protection was partial. Overall, DRDE-30 (propyl analogue) followed by DRDE-35 (butyl analogue) are favored as safer and better compounds.

Sulfur mustard (SM) is a potent vesicant, known for its ability to cause incapacitation and prolonged injuries to the eyes, skin and respiratory system. The toxic ocular events following sulfur mustard exposure are characterized by several stages: photophobia starting a few hours after exposure, an acute injury phase characterized by inflammation of the anterior segment and corneal erosions and a delayed phase appearing following a clinically silent period (years in human). The late injury appeared in part of the exposed eyes, expressed by epithelial defects and corneal neovascularization (NV), that lead to vision deficits and even blindness. During the last years /the authors/ have characterized the temporal development of ocular lesions following SM vapor exposure in rabbits and have shown the existence of two sub-populations of corneas, those exhibiting delayed ocular lesions (clinically impaired) and those exhibiting only minor injuries if at all (clinically non-impaired). The aim of the present study was to investigate the pathological mechanism underlying the delayed injury by focusing on the unique characteristics of each sub-population and to test the efficacy of potential treatments. Clinically impaired corneas were characterized by chronic inflammation, increased matrix metalloproteinase (MMP) activity, poor innervation and limbal damage. Moreover, using impression cytology and histology, we identified the delayed lesions as typical for an ocular surface disorder under the category of limbal epithelial stem cell deficiency (LSCD). These results point to therapeutic directions, using anti-inflammatory drugs, MMPs inhibitors, neurotrophic factors and amniotic membrane transplantation. Topical anti-inflammatory drugs, either steroid (Dexamycin, DEX) or non-steroidal anti-infllammatory drug (NSAID, Voltaren Ophtha) were found to be beneficial in ameliorating the initial inflammatory response and in postponing the development of corneal NV, when given during the first week after exposure. When DEX was administered as a symptomatic treatment against NV, a significant regression in the angiogenic process was observed, however, the effect was temporal and blood vessels reappeared after therapy ceased. Chronic administration (8 weeks) of the MMP inhibitor Doxycycline was also effective in attenuation of the acute and delayed injury. Preliminary results, using amniotic membrane transplantation revealed some decrease of corneal edema with no effect on corneal NV. It is suggested that the chronic inflammation and prolonged impairment of corneal innervation are playing a role in the pathogenesis of the delayed LSCD following SM exposure by creating a pathological microenvironment to limbal epithelial stem cells, thus, leading to their slow death and to a second cascade of pathological events eventually resulting in severe long-term injuries. As of today, only topical anti-inflammatory drugs reached the criteria of an applicable efficient post-exposure ocular treatment for SM injuries.

... Exposure of animals under halothane anesthesia to the chemical warfare agent sulfur mustard (HD; 1 mg/kg intravenous) produced mild signs of systemic intoxication during the subsequent 5 hours. Induction doses of ketamine 1 hour after HD exposure resulted in periods of profound apnea, with continued respiratory distress for the next 2 hours. When animals were treated with HD 1 hour after the initiation of ketamine anesthesia, severe and persistent convulsion-like muscular activity was observed within 45 minutes of HD administration. This nonpurposeful activity was not ameliorated by diazepam but was dramatically reduced or eliminated by resumption of halothane anesthesia. Treatment of HD-intoxicated pigs with succinylcholine produced a prolonged apnea resulting in death. In these apparently mildly HD-intoxicated animals, the introduction of ketamine or succinylcholine can rapidly induce potentially life-threatening situations.

For more Interactions (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (12 total), please visit the HSDB record page.

Target OrgansCancer, Developmental (effects during periods when organs are developing) , Gastrointestinal (Digestive), Lymphoreticular (Lymphoid), Ocular (Eyes), Reproductive (Producing Children), Respiratory (From the Nose to the Lungs)
Environmental Fate · 5 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a structure estimation method(2), indicates that bis(2-chloroethyl)sulfide is expected to have moderate mobility in soil(SRC). Bis(2-chloroethyl)sulfide has been observed to bind to dry soil through a reversible interaction mechanism(3). Volatilization of bis(2-chloroethyl)sulfide from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.45X10-5 atm-cu m/mole(4). Bis(2-chloroethyl)sulfide evaporates from dry soil and sand surfaces(5). At moderate temperatures (25 °C), bis(2-chloroethyl)sulfide deposited on the surface of soil has been reported to evaporate within 30 to 50 hours, depending on weather conditions(6). Evaporation rates can vary widely depending on temperature, surface type, wind and other factors(5-7); however, a primary dissipation mechanism for bis(2-chloroethyl)sulfide from soil is evaporation(8). Hydrolysis is an important process in moist soil environments; however, bis(2-chloroethyl)sulfide's low dissolution rate hinders the hydrolysis process(9). Bis(2-chloroethyl) hydrolyzes rapidly in distilled water with a half-life on the order of 4 to 8 minutes at 25 °C(8); however, in addition to the very low rate of dissolution, intermediate hydrolysis products and/or water-insoluble thickners can coat or encapsulate bis(2-chloroethyl)sulfide droplets and retard hydrolysis(8). In the absence of water, bis(2-chloroethyl)sulfide can react at higher temperatures in soil to form adducts and polymers(10); it is possible that polymer formation may result in entrapment of bis(2-chloroethyl)sulfide droplets and protection from subsequent dissolution and degradation(SRC). Soil microorganisms capable of degrading bis(2-chloroethyl)sulfide have been isolated and identified(11). However, after application to soil, bis(2-chloroethyl)sulfide degradation occurs mainly through chemical hydrolysis with microbiological degradation being the important fate process for degradation of the hydrolysis products that include thiodiglycol(11). Although bis(2-chloroethyl)sulfide can hydrolyze rapidly and evaporate from soil surfaces, the compound may persist in the soil environment for many years, or even decades(12). Its persistence in soil was realized as French soil contaminated in 1917 was found to contain bis(2-chloroethyl)sulfide for a number of years after 1917(12). In another instance, soldiers allowed into an area deemed safe from bis(2-chloroethyl)sulfide contamination were burnt while digging the soil even though bis(2-chloroethyl)sulfide was not used in that area in 3 years(10).

TERRESTRIAL FATE: The persistence in five soils ranged from 27 to 68 hr, with sand having the longest persistence and gravelly soil the least(1). At 0 °C the respective persistence times were 63.8, 72.6, 92.3, 49.7 days(2).

TERRESTRIAL FATE: The nature of the terrain has an important bearing on the behavior of the contaminant. Evaporation from grassland will be more rapid than from a permeable surface such as sand(1). In a field experiment designed to simulate a chemical attack, a small sample of bis(2-chloroethyl)sulfide was placed on top of the snow surface; another sample was immediately covered with 5 cm of snow in order to simulate a snowfall after an attack(2). Less than 0.1% of the bis(2-chloroethyl)sulfide was found after 14 days in both the uncovered and snow-covered samples. None of the agents studied, including bis(2-chloroethyl)sulfide, tended to migrate into the snow. Another investigator reported a persistence of 56 days in snow at -10 °C(3). In view of the fact that snow samples are quite variable, this value is not necessarily in conflict with the first (14 day) result. It has been suggested that bis(2-chloroethyl)sulfide may react in warm, dry soil to form 1,2-bis(2-chloroethylthio)ethane and higher adducts(4); however, no experimental evidence of such reactions have been reported(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Sulfur mustard can be absorbed into the body by inhalation, ingestion, skin contact, and eye contact. Inhalation is an important route of exposure. Ingestion is an uncommon route of exposure. Warm, moist areas with thin skin, the moist linings of body passages and cavities (mucous membranes), and perspiration-covered skin are more sensitive to the blistering (vesicant) effects of sulfur mustard.

Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ Chemical warfare agents (CWAs) have been disposed of in various fashions over the past decades. Significant amounts of CWA, roughly 11,000 ton, have been dumped in the Baltic Sea east of the island Bornholm following the disarmament of Germany after World War II. This has caused concerns over potential human and environmental health risks, and resulted in restrictions on fishing in the dumpsite area. The purpose of this paper is to assess the potential indirect human health risks due to consumption of CWA-contaminated fish from the dumpsite area east of Bornholm. Earlier studies suggest that the fish community may be at risk from CWA exposure in the Bornholm basin. Moreover, elevated frequencies of lesions on fish caught in a CWA dumpsite in the Mediterranean Sea have been observed. The fish at the Mediterranean dumpsite had elevated total arsenic (As) concentrations in their tissue, and elevated total As levels were also observed in the sediment. Elevated total sediment As concentrations have also been recorded in CWA dumpsites in the Skagerrak and the Baltic Sea. Triphenylarsine and sulfur mustard gas (Yperite) are the CWAs with the greatest indirect human health risk potential. There are recognized uncertainties concerning Yperite's and CWA-derived arsenical's fate and speciation in the environment, as well as their inherent toxicity, warranting caution and further site-specific environmental and human health risk assessments of CWAs dumped in the Bornholm basin.

Signs and Symptoms · 6 件

Cough. Burning sensation. Sore throat. Shortness of breath. Laboured breathing. Symptoms may be delayed.

MAY BE ABSORBED! Pain. Redness. Blisters. Serious skin burns.

Watering of the eyes. Redness. Pain. Severe deep burns. Loss of vision.

Abdominal pain. Nausea. Vomiting. Burning sensation. Shock or collapse. See Inhalation.

- Mild (onset within 4 to 12 hours): Tear production (lacrimation), irritation, itching, burning, spasmodic blinking (blepharospasm), dryness or gritty feeling, and possible pinpoint pupils (miosis).

- Nausea, vomiting (emesis), pain, diarrhea, possible chemical burns of the gastrointestinal (GI) tract, and complete exhaustion (prostration).

Effluent Concentrations · 1 件

Bis(2-chloroethyl)sulfide has been identified as a pollutant at the Fort McClellan army base /Alabama/ as well as at Rocky Mountain Arsenal(1). For some time after July 1917, much of French soil in region of battle lines was contaminated with mustard gas. The average and maximum concentrations likely to have been produced under military engagements in the area of falling shells have been estimated to be 3 and 5 ppm, respectively(2).

ICSC Environmental DataIt is strongly advised not to let the chemical enter into the environment because it is persistent.
Medical Surveillance · 5 件

Mild conjunctivitis beginning more than 12 hours after exposure is unlikely to progress to a severe lesion. The patient should have a thorough eye examination (including a test for visual acuity). The patient should be treated with a soothing eye solution, such as Visine or Murine, sent home, and told to return if there is worsening. Conjunctivitis beginning earlier and other effects such as lid swelling and signs/symptoms of inflammation indicate a need for inpatient care and observation.

A small area of erythema beginning later than 12 hours after exposure is unlikely to progress to a significant lesion. The patient should be examined, treated with a soothing lotion, sent home, and instructed to return if progression occurs. A patient with a significant area of erythema or one seen earlier with a significant area of erythema with or without blistering should be admitted for further evaluation. ... Patients with a large area of second or third degree burns should be transferred to a Burn Unit for further care and reverse isolation.

Airway damage is a common cause of death. ... at the first sign of damage of the larynx or below, the patient should be intubated and transferred to the Critical Care Unit. Bronchodilators should be used if there are signs of bronchoconstriction; steroids might be used if the usual bronchodilators are not effective, but otherwise steroids are not of proven value. Daily sputum cultures should be done and systemic antibiotics should be begun with signs of infection and an identified organism. A chemical pneumonitis may occur in the first several days with infiltrates on X-ray, an increase in WBC, and a fever, but this is generally sterile. Organisms generally are not the cause until the third or fourth day postexposure, and antibiotics should not be used prophylactically. Patients with airway damage below the pharynx should be managed on the Critical Care Unit by a physician experienced in the management of complicated pulmonary and airway injuries.

If the bone marrow has been damaged, the white blood cell count in the peripheral blood will start to decrease at about days 3 to 5 after exposure. This decrease may be followed by a decrease in red blood cells and platelets. ... A patient with a marked decrease in white blood cell count should be transferred to an Oncology or Burn Unit for reverse isolation.

For more Medical Surveillance (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (7 total), please visit the HSDB record page.

法規制情報

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Mustard gas is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

DHS Chemicals of Interest (COI) · 4 件

Sulfur mustard (Mustard gas (H))

CUM 100g

CUM 100g

Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

安全データ

tsca
TSCA listed
ridadr
2927
毒性
LD50 in rats, mice (mg/kg): 3.3, 8.6 i.v. (Anslow)
hazard_class
6.1(a)
packing_group
I
有毒物質データの
505-60-2(Hazardous Substances Data)

The biochemical sequelae to chloroethyl mustard exposure correspond very well to toxic processes initiated by free radicals. Additionally, mustard solutions contain spontaneously formed cyclic onium ions which produce carbon free radicals when reduced electrochemically. Therefore, /the authors/ hypothesized that the onium ions of sulfur or nitrogen mustards might produce carbon free radicals upon being reduced enzymatically, and that these radicals might constitute a metabolic activation. /The authors/ set out to document radical production using an in vitro metabolic system and electron paramagnetic resonance (EPR). /The/ system consisted of NADPH, one of several pyridine nucleotide-driven flavoprotein reductases, cytochrome c as a terminal electron acceptor, various sulfur or nitrogen mustards and the spin trap alpha-[4-pyridyl-1-oxide]-N-tert-butylnitrone in buffer. Reactions were started by adding the reductase to the other materials, vortexing and immediately transferring the mixture to a 10 mm EPR flat cell. Repeated scans on a Bruker ESP 300E EPR spectrometer produced a triplet of doublets with hyperfine splitting constants of a(N)=15.483 G and a(H)=2.512 G. The outcome supported /the/ hypothesis that carbon-centered free radicals are produced when mustard-related onium ions are enzymatically reduced. The EPR results varied little with the chloroethyl compound used or with porcine or human cytochrome P450 reductase, the reductase domain of rat brain neuronal nitric oxide synthase or rat liver thioredoxin reductase. /The/ results offer new insight into the basis for mustard-induced vesication and the outcome of exposure to different mustards. The free radical model provides an explanation for similarities in the lesions arising from mustard exposure and energy-based lesions such as those from heat, ultraviolet and nuclear radiation as well as damage across tissue types such as skin, eyes or airway epithelium.

Sulfur mustard (SM) is a strong alkylating agent, which produces subepidermal blisters, erythema and inflammation after skin contact. Despite the well-described SM-induced gross and histopathological changes, the exact underlying molecular mechanisms of these events are still a matter of research. As part of an international effort to elucidate the components of cellular signal transduction pathways, a large body of data has been accumulated in the last decade of SM research, revealing deeper insight into SM-induced inflammation, DNA damage response, cell death signaling, and wound healing. SM potentially alkylates nearly every constituent of the cell, leading to impaired cellular functions. However, SM-induced DNA alkylation has been identified as a major trigger of apoptosis. This includes monofunctional SM-DNA adducts as well as DNA crosslinks. As a consequence, DNA replication is blocked, which leads to cell cycle arrest and DNA single and double strand breaks. The SM-induced DNA damage results in poly(ADP-ribose) polymerase (PARP) activation. High SM concentrations induce PARP overactivation, thus depleting cellular NAD(+) and ATP levels, which in consequence results in necrotic cell death. Mild PARP activation does not disturb cellular energy levels and allows apoptotic cell death or recovery to occur. SM-induced apoptosis has been linked both to the extrinsic (death receptor, Fas) and intrinsic (mitochondrial) pathway. Additionally, SM upregulates many inflammatory mediators including interleukin (IL)-1alpha, IL-1beta, IL-6, IL-8, tumor necrosis factor-alpha (TNF-alpha) and others. Recently, several investigators linked NF-kappaB activation to this inflammatory response. This review briefly summarizes the skin toxicity of SM, its proposed toxicodynamic actions and strategies for the development of improved medical therapy.

For more Mechanism of Action (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (22 total), please visit the HSDB record page.

Biological Half-Life · 1 件

...in the rat, following a 6-hour cutaneous exposure to radiolabeled sulfur mustard with occlusion, the urinary excretion of radiolabel had a half-life of 1.4 days; the half-life of excretion in feces, which varied slightly with dose, was approximately 1.6 days. Most of the radioactivity was found in the urine. Most of the dose was eliminated by 3 days; however, measurable urinary excretion of radiolabel continued for >3 months.

Metabolism/Metabolites · 5 件

The metabolism of sulfur mustard has not been studied extensively. Sulfur mustard tends to undergo intramolecular cyclization to create a hyperactive compound. Conversion to this derivative is facilitated in aqueous solution, which accounts for the sensitivity of mucosal tissues, such as the eye, to its action. Sulfur mustard cyclic intermediates react with and alkylate electron-rich molecular structures, such as the sulfhydryl (-SH) and amino (-NH2) groups of proteins and nucleic acids. Metabolic pathways, including direct alkylation reactions, glutathione reactions, hydrolysis, and oxidation, are presumed based on the finding of sulfur mustard DNA adducts in tissues and the identification of urinary products. ... Thiodiglycol was also found in the urine of people exposed to airborne sulfur mustard during the Iran-Iraq. A sulfur mustard adduct in DNA, the 2'-deoxyguanosine derivative of N7-HETE-guanine, N7-(2-hydroxyethylthioethyl)-2'deoxyguanosine, as well as albumin- and hemoglobin-sulfur mustard adducts, have been detected in the blood of two sulfur mustard poisoning victims of the Iran-Iraq War. ....

Studies of casualties of the Iran-Iraq War with obvious signs of sulfur mustard-induced cutaneous injuries have identified significant amounts of the sulfur mustard metabolite, thiodiglycol, in human urine for up to 2 weeks after sulfur mustard exposure. ... DNA-, hemoglobin- and albumin-sulfur mustard adducts have been detected in the blood of sulfur mustard poisoning victims. In two subjects following an accidental predominantly cutaneous exposure to sulfur mustard, thiodiglycol, thiodiglycol sulfoxide, and closely related metabolites, 1,1'-sulfonylbis[2-(methylsulfinyl)ethane] and 1-methylsulfinyl-2-[2-methylthio) ethylsulfonyl]ethane, derived from the action of beta-lyase on cysteine conjugates, were detected in the urine. Thiodiglycol sulfoxide concentrations were 20 to 35 times thiodiglycol concentrations. The beta-lyase metabolites were detected at concentrations comparable with those of thiodiglycol sulphoxide

... the excretion of thiodiglycol in human urine /was measured/ following an accidental exposure to sulfur mustard vapor and aerosol. Detectable levels of thiodiglycol in urine were measured for 13 days after exposure to an undetermined level. The patient's urine was randomly sampled for 6 months after exposure and no further thiodiglycol elimination was detected. Maximum thiodiglycol excretion was seen on postexposure day 4. First-order elimination kinetics was observed, and the half-life of thiodiglycol elimination was estimated to be 1.2 days.

After absorption, sulfur mustard undergoes intermolecular cyclization to form an ethylene episulfonium ion intermediate, liberating a free chloride anion.

For more Metabolism/Metabolites (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (11 total), please visit the HSDB record page.

MeSH Pharmacological Classification · 2 件

Chemicals that are used to cause the disturbance, disease, or death of humans during WARFARE.

Drugs used to treat or prevent skin disorders or for the routine care of skin.

Absorption, Distribution and Excretion · 5 件

It has been demonstrated that 80% of sulfur mustard applied to the skin evaporates, 10% remains in the skin and 10% gets absorbed systemically. It can penetrate the skin by contact with either the liquid or vapor. The rate of penetration is proportional to dose, temperature and humidity.

Levels of mustard in the tissues of an Iranian patient who died 7 days after exposure to mustard gas were qualitatively analysed. The concentrations of sulfur mustard determined by GC/MS and atomic absorption spectrophotometer in the tissues were as follows: fat (from thigh) 15.1 mg/kg; brain 10.7 mg/kg; abdominal skin 8.4 mg/kg; kidney 5.6 mg/kg; muscle 3.9 mg/kg; liver 2.4 mg/kg; cerebrospinal fluid 1.9 mg/L; spleen 1.5 mg/kg; blood 1.1 mg/L.

(35)S-labeled sulfur mustard diffused rapidly throughout the body after intravenous (IV) injection in experiments employing rabbits. Activity was retained chiefly in the liver, lungs, and kidneys, with approximately 20 percent of the (35)S activity being excreted in 12 hours.

... /The toxicokinetics of/ sulfur mustard (SM) ... as well as its major DNA-adduct were studied in male hairless guinea pigs for the intravenous, respiratory and percutaneous routes. The study comprised measurement of the concentration-time course of SM in blood and measurement of the concentrations of intact SM and its adduct to guanine in various tissues at several time points after administration of, or exposure to SM. ... In contrast with nerve agents of the phosphofluoridate type, SM partitions strongly to various organs, especially the lung, spleen, liver and bone marrow. The respiratory toxicity of SM appears to be local, rather than systemic. ...

For more Absorption, Distribution and Excretion (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (11 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Chemical warfare;

The principal use of sulfur mustard was as a vesicant chemical warfare agent.

Organic synthesis, poison gas, medicine

Medication: /Formerly/ used topically in the treatment of psoriasis.

Mustard gas was used as a vesicant in chem warfare during World War I & in Ethiopia in 1936 ...

In biological studies of alkylating agents

U.S. Production · 2 件

(1972) NOT PRODUCED COMMERCIALLY IN USA

(1975) NOT PRODUCED COMMERCIALLY IN USA

Methods of Manufacturing · 4 件

/It is/ prepared by treating ethylene with sulfur chloride (Levinstein process) ... by treating beta, beta'-dihydroxyethyl sulfide with hydrogen chloride gas (German process).

... From thiodiglycol and hydrogen chloride.

The Germans produced sulfur mustard using the Meyer process, which involved treating ethylene with hypochlorous acid followed by sodium sulfide, yielding beta,beta'-dihydroxy-methyl sulfide. This in turn was heated with hydrochloric acid, which produced sulfur mustard. In the United States, sulfur mustard was formerly made using the Levenstein process in which ethylene was reacted with sulfur monochloride at 30-35 °C. Sulfur mustard produced by this process contains 62-64% distilled sulfur mustard (or HD). The most recent process used in the United States involved the formation of bis-(2-hydroxyethyl)-thioether from ethylene oxide and hydrogen sulfide; this was then reacted with hydrochloric acid to form sulfur mustard. Sulfur mustard produced by this process contains 89% HD.

Synthesis: 1) thiodiglycol and gaseous HCl; 2) sulfur monochloride and dry ethylene; 3) sulfur monochloride and pure ethylene; 4) sulfur dichloride in carbon tetrachloride and ethylene; 5) sulfur monochloride and ethylene saturated with alcohol.

Formulations/Preparations · 2 件

Grades: pure; technical (containing excess sulfur as a polysulfide)

Commercial production results in the formation of a mixture containing about 70% bis(2-chloroethyl)sulfide and about 30% high molecular weight polysulfides.

Use ClassificationChemical Classes -> Warfare and Terrorism Agents (used in acts of war or terror)
General Manufacturing Information · 6 件

Ethane, 1,1'-thiobis[2-chloro-: ACTIVE

Bis(2-chloroethyl)sulfide is listed in the CWC /Chemical Weapons Convention/ Annex on Chemicals under Schedule 1.

/The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 1 lists chemicals considered to pose a high risk to the object and purpose of the Convention by virtue of their high potential for use in activities prohibited by the CWC. These chemicals have little or no use for peaceful purposes in commercial or industrial trade. ... Schedule 1 also lists precursor chemicals that may be used in the final single technological stage of production of any of the toxic chemicals listed in the schedule

The term "Mustard gas" refers to several manufactured chemicals, including sulfur mustard. They are not naturally occurring in the environment. Mustard gas does not behave as a gas under normal conditions.

HD is distilled sulfur mustard which has been purified by washing and vacuum distillation. H is Levenstein mustard which contains about 30% sulfur impurities and has a stronger vesicant action. HT consists of 60% HD and 40% T /bis(2-chloroethylthioethyl)ether/ (a related vesicant with lower freezing point and much lower volatility), with reportedly similar characteristics to HD.

For more General Manufacturing Information (Complete) data for BIS(2-CHLOROETHYL)SULFIDE (6 total), please visit the HSDB record page.

応用分野 · 5 件

解説マスタードガス.イペリットともいう.硫化ジ(2-クロロエチル)の慣用名.エチレンと塩化硫黄から得られる.蒸気圧の低い,無色,無臭の液体.不純なものは臭いがある.融点13~14 ℃,沸点215 ℃.d204 1.2741.n20D 1.53125.水に微溶,有機溶媒に可溶.アルカリにより加水分解される.酸化剤によりスルホキシドまたはスルホンを与える.毒性が強く,皮膚,毛細管,赤血球をおかす.高濃度の場合は皮膚から吸収され,内臓をもおかす.発がん性があり,DNAをアルキル化し,二本鎖に架橋を生じる.有機合成原料として用いられる.LD50 3.3 mg(ラット,静注).

用途第1次大戦、ならびにイランイラク戦争で化学兵器(毒ガス)に使用、少量がアルキル化剤のモデル物質として研究材料に利用、抗がん剤として検討されたが高い毒性ため成功しなかった、医学分野において角質細胞(PSORATIC KERATINOCYTES)の過剰増殖調整剤として使用される。

説明Mustard gas/sulphur mustard is an organic chemical substance synthesised by treating sulphur dichloride with ethylene. Mustard gas is a chemical substance closely related to chemical warfare class agents. It is a cytotoxic and vesicant chemical substance, and exposures are known to cause blisters on the exposed skin. Pure mustard gas/sulphur mustards are colourless, viscous liquids at room temperature. However, when used in impure form, such as warfare agents, they appear as yellow brown in colour. As the name indicates, mustard gas has an odour resembling the garlic, horseradish, or mustard plants. Mustard gas is the common name given to 1,1-thiobis(2-chloroethane), a chemical warfare agent that is believed to have first been used near Ypres in Flanders on 12 July 1917. Mustard gas is a thick liquid at ambient temperature. It is heavier than water as a liquid and heavier than air as a vapour. It does not occur naturally in the environment. Pure liquid mustard gas is colourless and odourless. It is stable, combustible, and incompatible with strong oxidising agents. Mustard gas on mixing with other chemical substances appears brown in colour and gives off a garlic-like smell. When heated, it decomposes and emits highly toxic, corrosive fumes and fumes of oxides of sulphur and chlorine-containing compounds. It is soluble in fats and oils, gasoline, kerosene, acetone, carbon tetrachloride, alcohol, tetrachloroethane, ethylbenzoate, and ether, and solubility in water is negligible. It is miscible with the OP nerve agents. During earlier years, mustard gas was in use as an important chemical warfare agent. In fact, it was used in large amounts during World Wars I and II. Mustard gas was first used by the German army in 1917. It was one of the most lethal of all the poisonous chemicals used during the war. It was reportedly used in the Iran–Iraq war in 1980–1988. It is not presently used in the United States, except for research purposes.

使用Formerly in chemical warfare. In biological studies of alkylating agents.

一般的な説明Mustard gas is a clear amber colored oily liquid with a faint odor of mustard/garlic. Mustard gas is not readily combustible. Its vapors are heavier than air, are very toxic, and can be absorbed through the skin. The effects from exposure to the material include blindness which may be delayed. Prolonged exposure of the container to fire or intense heat may cause Mustard gas to violently rupture and rocket. Mustard gas is also known as dichlorodiethyl sulfide.

上流・下流製品情報

上流原料

二酢酸チオジエチレンシアノぎ酸クロリドBIS(2-CHLOROETHYL)TRISULPHIDECarbonocyanidic fluorideBIS(2-CHLOROETHYL)DISULPHIDEアセチルクロリドエテン

下流製品

2-Chloroethyl vinyl sulfideビニルチオエテン2-chloroethanethiol1,1,1,2-テトラクロロエタン (1mg/mlメタノール溶液) [水質分析用]

補足説明

定義ChEBI: An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a structure estimation method(2), indicates that bis(2-chloroethyl)sulfide may adsorb moderately to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.45X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 49 hours and 19 days, respectively(SRC). Hydrolysis is an important process in aquatic environments. Bis(2-chloroethyl)sulfide hydrolyzes rapidly in distilled water with a half-life on the order of 4 to 8 minutes at 25 °C(5); however, hydrolytic destruction can be limited by a very low rate dissolution into the water(5,6). Experimental data measured hydrolysis in water, as a function of temperature; bis(2-chloroethyl)sulfide hydrolyzed in 1.5 to 158 mins at 40-0.6 °C(7,8). Hydrolysis in seawater varies greatly with the temperature of the water and the depth of the chemical in the water(9). At the very bottom, bis(2-chloroethyl)sulfide will be found in the solid form; a one ton solid cylinder of bis(2-chloroethyl)sulfide would take about 5 yr to dissolve. In the water column of a body of seawater, dissolved bis(2-chloroethyl)sulfide will be lost by hydrolysis with its half-life ranging from 15 min at 25 °C to 175 min at 5 °C. According to a classification scheme(10), an estimated BCF of 12(SRC), from an estimated log Kow of 2.14(2), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-chloroethyl)sulfide, which has a vapor pressure of 0.11 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase bis(2-chloroethyl)sulfide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 days(SRC), calculated from its rate constant of 7.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The principal UV absorption band of bis(2-chloroethyl)sulfide in cyclohexane is at 205 nm; a very weak band occurs around 280 nm and has a tail that extends just beyond 300 nm(4). This indicates that direct photolysis, while possible, is not likely to be an important mode of degradation. Vapor-phase bis(2-chloroethyl)sulfide is relatively stable to hydrolysis in moist air, but the vapors can be adsorbed into liquid-phase water which results in hydrolysis(5).