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O-Mustard

HCID 45452
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
63918-89-8
Standard SMILES
ClCCSCCOCCSCCCl
InChIKey
FWVCSXWHVOOTFJ-UHFFFAOYSA-N
Molecular formula
C8H16Cl2OS2
Average molar mass
263.2 g/mol
Monoisotopic mass
262.0019629

Overview

This is a chemical weapon related to sulfur mustard (mustard gas) and is expected to react in a similar fashion. See the chemical datasheet for sulfur mustard for more information.

Names & identifiers

Preferred name
O-Mustard
IUPAC
1-(2-chloroethylsulfanyl)-2-[2-(2-chloroethylsulfanyl)ethoxy]ethane
English name
Bis(2-(2-chloroethylthio)ethyl)ether
Molecular formula
C8H16Cl2OS2
Molecular weight
263.25

Names & synonyms

O-MustardAgent TO-Mustard TBis(2-chloroethylthioethyl) etherO-Mustard (T)ETHER, BIS(2-CHLOROETHYLTHIOETHYL)NSC 588182-2'-Di(3-chloroethylthio)-diethyl etherBis(beta-chloroethylthioethyl) etherEthane, 1,1'-oxybis(2-(2-chloroethyl)thio-BRN 1752929bis(2-chloroethylthioethyl)ether
Show more names
FWVCSXWHVOOTFJ-UHFFFAOYSA-NBis(2-(2-chloroethylthio)ethyl)etherEthane, 1,1'-oxybis[2-[(2-chloroethyl)thio]-Bis(2-chlorethylthioethyl) ether: (2-2'-Di(3-chloroethylthio)diethyl ether
DTXSID7074799HSDB 83983-01-00-02126 (Beilstein Handbook Reference)Ethane, 1,1'-oxybis[2-(2-chloroethyl)thio-RefChem:855298DTXCID904416263918-89-8NSC-58818

Database identifiers

CAS
63918-89-8
PubChem CID
45452
DTXSID
DTXSID7074799

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
59.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
10
Heavy atoms
13
Formal charge
0
Complexity
86.2

Experimental & physicochemical properties

OdorGarlic-like odor
Density1.24 g/mL at 25 °C
Color/Form · 3 items

Sulfur mustards are colorless when pure, but are typically yellow to brown oily liquids. /Sulfur mustards/

Sulfur mustards can be clear to yellow or brown when in liquid or solid form. /Sulfur mustards/

Powder

Solubility · 2 items

Sulfur mustards, including Agent T (O-Mustard), do not dissolve much in water, but dissolve easily in oils, fats, and other solvents. /Sulfur mustards/

Although sulfur mustards have limited solubility in water at neutral pH, the small quantity that dissolves is reactive. /Sulfur mustards/

Boiling Point · 2 items

Decomposes

BP: 120 °C at 0.0225 mm Hg; Volatility: 2.8 mg/cu m at 25 °C

Decomposition · 2 items

When heated to decomposition it emits very toxic fumes of SOx and Cl-

We include in this review an assessment of the formation, environmental fate, and mammalian and ecotoxicity of chemical warfare (CW) agent degradation products relevant to environmental and occupational health. These parent CW agents include several vesicants: sulfur mustards [undistilled sulfur mustard (H), sulfur mustard (HD), and an HD/agent T mixture (HT)]; nitrogen mustards [ethylbis(2-chloroethyl)amine (HN1), methylbis(2-chloroethyl)amine (HN2), tris(2-chloroethyl)amine (HN3)], and Lewisite; four nerve agents (O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothioate (VX), tabun (GA), sarin (GB), and soman (GD)); and the blood agent cyanogen chloride. The degradation processes considered here include hydrolysis, microbial degradation, oxidation, and photolysis. We also briefly address decontamination but not combustion processes. Because CW agents are generally not considered very persistent, certain degradation products of significant persistence, even those that are not particularly toxic, may indicate previous CW agent presence or that degradation has occurred. Of those products for which there are data on both environmental fate and toxicity, only a few are both environmentally persistent and highly toxic. Major degradation products estimated to be of significant persistence (weeks to years) include thiodiglycol for HD; Lewisite oxide for Lewisite; and ethyl methyl phosphonic acid, methyl phosphonic acid, and possibly S-(2-diisopropylaminoethyl) methylphosphonothioic acid (EA 2192) for VX. Methyl phosphonic acid is also the ultimate hydrolysis product of both GB and GD. The GB product, isopropyl methylphosphonic acid, and a closely related contaminant of GB, diisopropyl methylphosphonate, are also persistent. Of all of these compounds, only Lewisite oxide and EA 2192 possess high mammalian toxicity. Unlike other CW agents, sulfur mustard agents (e.g., HD) are somewhat persistent; therefore, sites or conditions involving potential HD contamination should include an evaluation of both the agent and thiodiglycol.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Reactive GroupEthers
Reactivity AlertsWater-Reactive
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Other Hazardous ReactionsSulfur mustards are rapidly corrosive to brass and steel at 149 °F (65 °C); they are destroyed by strong oxidizing agents. These agents hydrolyze to form hydrochloric acid (HCl) and thiodiglycol.
DHS Chemicals of Interest (COI) · 4 items

O-Mustard (T)

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.

Safety & protection

Disposal Methods · 1 item

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Preventive MeasuresPeople whose skin or clothing is contaminated with sulfur mustard can contaminate rescuers by direct contact or through off-gasing vapor. /Sulfur mustard/
Protective Action Criteria (PAC) · 3 items

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Warfare and Terrorism Agents

Delayed-action casualty agent. /Mustard-T Mixture (HT)/

Methods of ManufacturingSynthesis: 1) bis(2-hydroxyethylthioethyl)ether and thionyl chloride; 2) bis(2-mercaptoethyl)ether and vinyl chloride; 3) thiodiglycol and bis(2-hydroxyethyl)sulfide with HCl; 4) thiodiglycol and NaOH and bis(2-chloroethyl)sulfide.
Formulations/PreparationsAgent HT is generally a mixture of 60% HD /distilled mustard or bis(2-chloroethyl)sulfide/ and 40% bis(2-chloroethylthioethyl)ether (T), although this ratio may vary.
General Manufacturing Information · 4 items

O-Mustard 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.

Sulfur mustards H/HD and HT are manufactured compounds. They are colorless when pure, but are typically yellow to brown oily liquids with a slight garlic or mustard odor. Agent H contains about 20-30% impurities. The nearly pure substance is called HD. HT is a mixture of 60% HD and 40% of another substance called agent T. They do not dissolve much in water, but dissolve easily in oils, fats, and other solvents. They are stable at ambient temperatures. Sulfur mustards were introduced as chemical warfare agents during World War I. More than a dozen countries have sulfur mustard agents in their chemical arsenals. Destruction of U.S. stockpiles of chemical agents, including sulfur mustards, was mandated by the Chemical Weapons Convention to take place before April 2007.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
BG8SN2S6WA
Nikkaji
J92.984K
Melting Point45 °C
Vapor Pressure3X10-6 mm Hg at 25 °C
Physical DescriptionThis is a chemical weapon related to sulfur mustard (mustard gas) and is expected to react in a similar fashion. See the chemical datasheet for sulfur mustard for more information.
Other Experimental Properties · 3 items

When heated to decomposition it emits very toxic fumes of SOx and Cl-.

No rapid reaction with air. No rapid reaction with water, but is water reactive.

O-Mustard (Agent T) has a much lower volatility than mustard gas and a lower vapor pressure than sulfur mustard which makes it inefficient as a respiratory agent by itself. It can be mixed with sulfur mustard to make Agent HT.

Physicochemical properties

Boiling point
174 °C · 174 °C(Press: 2 Torr)
Density
1.203 · 1.2030 (estimate)
FDA UNII
8 SN2S6WA · BG8SN2S6WA
EPA Substance Registry System
O-Mustard (T) (63918-89-8)
Hazardous Substances Data
63918 · 63918-89-8(Hazardous Substances Data)

0.12 [mg/m3]

1.3 [mg/m3]

7.6 [mg/m3]

Personal Protective Equipment (PPE) · 3 items

Skin/ocular protection: Personal protective equipment (PPE) and butyl rubber chemical-protective gloves are recommended at all times when these chemicals are suspected to be involved. /Sulfur mustards/

Respiratory protection: Pressure-demand, self-contained breathing apparatus (SCBA) is recommended in response situations that involve exposure to any amount of sulfur mustard. /Sulfur mustards/

MOPP4 /All protection worn/ whenever liquid or vapor is present. /Mustard-T Mixture (HT)/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1180(SRC), determined from a structure estimation method(2), indicates that O-Mustard is expected to have low mobility in soil(SRC). Volatilization of O-Mustard from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). The Sulfur Mustards, including Agent T (O-Mustard), do not dissolve much in water(3), but the small quantity that dissolves is reactive(4). The hydrolysis half-life of dissolved O-Mustard was determined to be 2.8 minutes at 25 °C(5). O-Mustard is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3X10-6 mm Hg at 25 °C(6). Biodegradation data in soil were not available(SRC, 2017).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1180(SRC), determined from a structure estimation method(2), indicates that O-Mustard is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). The Sulfur Mustards, including Agent T (O-Mustard), do not dissolve much in water(4), but the small quantity that dissolves is reactive(5). The hydrolysis half-life of dissolved O-Mustard was determined to be 2.8 minutes at 25 °C(6). According to a classification scheme(7), an estimated BCF of 28(SRC), from an estimated log Kow of 2.71(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2017).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), O-Mustard, which has a vapor pressure of 3X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase O-Mustard 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 5.2 hours(SRC), calculated from its rate constant of 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase O-Mustard may be removed from the air by wet and dry deposition(SRC).

Toxicity Summary · 1 item

IDENTIFICATION AND USE: O-Mustard is colorless when pure but is typically a yellow to brown oily substance with a slight garlic or mustard odor. This is a warfare and terrorism agent. HUMAN STUDIES: High doses of sulfur mustards can cause hyperexcitability, convulsions, and insomnia. The eye is the most sensitive tissue to sulfur mustard effects. Sulfur mustard vapor or liquid may cause intense conjunctival and scleral pain, swelling, lacrimation, blepharospasm, and photophobia; however, these effects do not appear for an hour or more. Miosis due to cholinergic effects may occur. High concentrations of vapor or liquid can cause corneal edema, perforation, blindness, and later scarring. Direct skin exposure to sulfur mustards causes erythema and blistering. Generally, a pruritic rash will develop within 4 to 8 hours followed by blistering 2 to 18 hours later. Contact with the vapor may result in first and second degree burns, while contact with the liquid typically produces second and third degree chemical burns. An area of burn covering 25% or more of the body surface area may be fatal. Ingestion may cause chemical burns of the GI tract and cholinergic stimulation. Nausea and vomiting may occur following ingestion or inhalation. Early nausea and vomiting is usually transient and not severe. Nausea, vomiting, and diarrhea occurring several days after exposure indicates damage to the GI tract and thus is a poor prognostic sign. Dose-dependent inflammatory reactions in the upper and lower airway begin to develop several hours after exposure and progress over several days. Burning nasal pain, epistaxis, sinus pain, laryngitis, loss of taste and smell, cough, wheezing, and dyspnea may occur. Necrosis of respiratory epithelium can cause pseudomembrane formation and local airway obstruction. Death usually occurs between 5 and 10 days due to pulmonary insufficiency complicated by infection due to immune system compromise. Systemic absorption of sulfur mustard may induce bone marrow suppression and an increased risk for fatal complicating infections, hemorrhage, and anemia. Years after apparent healing of severe eye lesions, relapsing keratitis or keratopathy may develop. Prolonged or repeated acute exposure to sulfur mustards may cause cutaneous sensitization and chronic respiratory disease. ANIMAL STUDIES: There are no data available.

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of O-Mustard can be estimated to be 1180(SRC). According to a classification scheme(2), this estimated Koc value suggests that O-Mustard is expected to have low mobility in soil.

Human Toxicity Excerpts · 5 items

/SIGNS AND SYMPTOMS/ Eyes are very susceptible to low concentrations; incapacitating effects by skin absorption require higher concentrations than does eye injury. /Mustard-T Mixture (HT)/

/SIGNS AND SYMPTOMS/ It is somewhat more vesicant than Levinstein mustard (H) on bare skin; however, it is less vesicant through wet or dry clothing and is somewhat less effective than H on the eyes. /Mustard-T Mixture (HT)/

/SIGNS AND SYMPTOMS/ Death usually occurs between the 5 and 10 day due to pulmonary insufficiency complicated by infection due to immune system compromise. /Sulfur mustards/

/SIGNS AND SYMPTOMS/ The eye is the most sensitive tissue to sulfur mustard effects. Sulfur mustard vapor or liquid may cause intense conjunctival and scleral pain, swelling, lacrimation, blepharospasm, and photophobia; however, these effects do not appear for an hour or more. Miosis due to cholinergic effects may occur. High concentrations of vapor or liquid can cause corneal edema, perforation, blindness, and later scarring. /Sulfur mustards/

For more Human Toxicity Excerpts (Complete) data for O-Mustard (16 total), please visit the HSDB record page.

Artificial Pollution Sources · 1 item

O-Mustard's limited production for research may result in its release to the environment through various waste streams; its illegal use as a chemical warfare agent(1,2) will result in its direct release to the environment(SRC). Destruction of US stockpiles of chemical agents, including sulfur mustards, was mandated by the Chemical Weapons Convention to take place before April 2007(2).

Sediment/Soil Concentrations · 1 item

In August 1988, chemical weapons were reported used against Kurdish populations in the mountainous region of northern Iraq close to the borders of Turkey and Iran(1). In November of that year, soil samples (and other samples) were collected from a hillside site of an impacted bomb(1). Analysis of the soil samples identified degradation products of sulfur mustard and O-mustard(1).

Environmental Bioconcentration · 1 item

An estimated BCF of 28 was calculated in fish for O-Mustard(SRC), using an estimated log Kow of 2.71(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for O-Mustard is estimated as 3.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that O-Mustard is expected to be essentially nonvolatile from water surfaces(2). In addition, any O-Mustard that dissolves into water will be reactive with the water(3). O-Mustard's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). O-Mustard is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3X10-6 mm Hg at 25 °C(4).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of O-Mustard with photochemically-produced hydroxyl radicals has been estimated as 7.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The apparent hydrolysis half-life of O-Mustard at 25 °C was determined to be 2.8 minutes in an aqueous solution containing 5% ethanol at pH of 5-8(1).

Probable Routes of Human ExposureOccupational exposure to O-Mustard may occur through inhalation and dermal contact with this compound at workplaces where O-Mustard is produced or used. (SRC)
Other Environmental ConcentrationsO-Mustard decontamination derivatives were detected in decontamination waste from chemical weapons (CW) agents stored in containers on Johnston Atoll (US territory located in the Pacific Ocean) since 1971(1).
Environmental Fate/Exposure Summary · 1 item

O-Mustard's limited production for research may result in its release to the environment through various waste streams; its illegal use as a chemical warfare agent will result in its direct release to the environment. Destruction of US stockpiles of chemical agents, including sulfur mustards, was mandated by the Chemical Weapons Convention to take place before April 2007. If released to air, a vapor pressure of 3X10-6 mm Hg at 25 °C indicates O-Mustard will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase O-Mustard will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 5.2 hours. Particulate-phase O-Mustard will be removed from the atmosphere by wet and dry deposition. If released to soil, O-Mustard is expected to have low mobility based upon an estimated Koc of 1180. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 3.8X10-8 atm-cu m/mole. O-Mustard is not expected to volatilize from dry soil surfaces based upon its vapor pressure. O-Mustard does not dissolve much in water, but the quantity that dissolves is reactive indicating that hydrolysis in moist soil is an important fate process. Biodegradation data in soil or water were not available. If released into water, O-Mustard is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. O-Mustard that dissolves in water has a hydrolysis half-life of 2.8 minutes at 25 °C. Occupational exposure to O-Mustard may occur through inhalation and dermal contact with this compound at workplaces where O-Mustard is produced or used. (SRC)

Regulatory information

DHS Chemicals of Interest (COI) · 4 items

O-Mustard (T)

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.

Safety data

Hazardous Substances Data
63918-89-8(Hazardous Substances Data)

In the period following World War I and during World War II, a wide variety of sulfur analogues of mustard were investigated and many potent vesicants were discovered. Each had two 2-chloroethyl groups attached to a sulfur atom. Examples of such compounds are 1,2-bis(2-chloroethylthio)ethane (Chemical Agent Symbol Q), ... and bis(2-chloroethylthioethyl) ether (T), ... . It is noteworthy that each 2-chloroethyl group is associated with a separate sulfur atom, not with the same one as for mustard. Both Q and T are more vesicant than mustard, but neither is as volatile. For that reason, neither is as effective by the vapor route.