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클로로아세틸 클로라이드

Chloroacetyl chloride

HCID 6577
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
79-04-9
표준 SMILES
O=C(Cl)CCl
InChIKey
VGCXGMAHQTYDJK-UHFFFAOYSA-N
분자식
C2H2Cl2O
평균 분자량
112.94 g/mol
단동위원소 질량
111.94827004

개요

Chloroacetyl chloride appears as a colorless to light yellow liquid with a very pungent odor. Very toxic by inhalation. Corrosive to metals and tissue.

이름 및 식별자

우선 이름
Chloroacetyl chloride
IUPAC
2-chloroacetyl chloride
현지명
클로로아세틸 클로라이드
영어명
Chloroacetyl chloride
분자식
C2H2Cl2O
분자량
112.94

이름 및 동의어

CHLOROACETYL CHLORIDE79-04-92-chloroacetyl chlorideAcetyl chloride, chloro-Monochloroacetyl chlorideChloracetyl chlorideChloroacetic chlorideChloroacetic acid chlorideChlorure de chloracetyleChlorid kyseliny chloroctoveDTXSID4026472K5UML06YUO
이름 더 보기
클로로아세틸클로라이드클로로아세틸염화물클로로아세틸클로라이드클로로아세틸 클로라이드2-클로로아세틸 클로라이드모노클로로아세틸 클로라이드아세틸 클로라이드, 2-클로로-아세틸 클로라이드, 클로로-클로로아세트산 클로라이드염화클로로아세틸chloroacetylalpha-Chloroacetyl chlorideCH2ClCOClChloroacetic ahloridechloracetylChloracetylchloridAcetylchloride,chloro-
DTXCID306472RefChem:125361201-171-6ChloroacetylChloridechloracetylchlorideMFCD00000725monochloroacetic acid chloridechloro acetyl chloride

데이터베이스 식별자

CAS
79-04-9
PubChem CID
6577
DTXSID
DTXSID4026472
ChEMBL
CHEMBL3187685
ChEBI
CHEBI:34624
UNII
K5UML06YUO
EC Number
201-171-6
Nikkaji
J1.490G

물성

구조 계산 물성보충 중

XLogP
1.4
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
5
형식 전하
0
복잡도
42.9

실험 및 물리화학적 성질

Chemical Classes · 2건

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesSchoenflies notation
Odor · 2건

Sharp, pungent, irritating

Strong, pungent odor.

Density · 6건

1.42 at 68 °F (USCG, 1999) - Denser than water; will sink

1.4202 g/cu cm at 20 °C

Density: 1.4202 at 20 °C/4 °C

Relative density (water = 1): 1.4

1.42

1.4202 @ 20°C

Color/Form · 4건

Liquid

Colorless liquid

Water-white liquid

Colorless to yellowish liquid.

Solubility · 6건

Decomposes (NIOSH, 2024)

Decomposed by water

Initially insoluble in water, however a slow reaction at the water-chloroacetyl chloride interface produces chloroacetic acid. When sufficient acid is formed to solubilize the two phases, a violent reaction forming chloroacetic acid and HCl occurs.

Miscible with ethyl ether; soluble in acetone, carbon tetrachloride.

Miscible with acetone and benzene.

Solubility in water: reaction

Corrosivity

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H290 (52.9%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P361+P364, P363, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

유해성 정보

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 5건

Chemical: Acetyl chloride, chloro-

Acetyl chloride, 2-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetyl chloride, 2-chloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 29-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13326

Chloroacetyl chloride: HSNO Approval: HSR002935 Approved with controls

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.)

DOT LabelPoison Inhalation Hazard Corrosive
Fire Hazards · 3건

Special Hazards of Combustion Products: Heat of fire can cause decomposition, with evolution of highly toxic and irritating hydrogen chloride and phosgene vapors.

· Combustible material: may burn but does not ignite readily.

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Oxidation of the vinyl halide carcinogen and hepatotoxin vinylidene chloride (VDC) by microsomal cytochrome p450 yields 2,2-dichloroacetaldehyde, 2-chloroacetyl chloride, 2-chloroacetic acid, and l,l-dichloroethylene oxide. The roles of these metabolites in covalent modification of proteins and reduced glutathione (GSH) were examined. 2-Chloroacetyl chloride reacted with model thiols at least 10(3)-fold faster than did l,l-dichloroethylene oxide and at least 10(5)-fold faster than did 2,2-dichloroacetaldehyde or 2-chloroacetic acid.

용도 및 제조

Uses · 6건

Used in organic synthesis; [ACGIH]

Toxic Gas from Spilling Chemical in Water [Category: Other]

In the synthesis of organic compounds.

Preparation of chloroacetophenone, intermediate, tear gas.

The chief use of chloroacetyl chloride (CAC) is as an intermediate in the manufacture of chloroacetophenone and other chemicals.

Much of the chloroacetyl chloride produced is used captively as a reactive intermediate. ... acylation reactions and in the production of adrenalin, diazepam, chloroacetophenone, chloroacetate esters and chloroacetic anhydride.

U.S. Production · 4건

2023: 40,000,000 - <55,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 4.54X10+5 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Chloroacetylchloride:

Consumption Patterns · 2건

Much of the chloroacetyl chloride produced is used captively as a reactive intermediate.

Estimated that the chloroacetyl chloride requirement for the manufacture of alachlor and butachlor was in excess of 45,000 metric tons in 1992. Significant volumes are also used in pharmaceutical manufacture, such as anesthetics of the lidocaine type, and in the production of the tear gas chloroacetophenone.

Industry Uses

관련 반응

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반응 기록 만들기
HRID 897 반응식
HRID 897반응물로uspto-grants-1998_03
HRID 1513 반응식
HRID 1513반응물로uspto-grants-1998_03
HRID 1581 반응식
HRID 1581반응물로uspto-grants-1998_03
HRID 2086 반응식
HRID 2086반응물로uspto-grants-1998_03
HRID 2127 반응식
HRID 2127반응물로uspto-grants-1998_03
HRID 2185 반응식
HRID 2185반응물로uspto-grants-1998_03
HRID 2703 반응식
HRID 2703반응물로uspto-grants-1998_03
HRID 3596 반응식
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
... metals (corrosive)
Flash Point100 °C (212 °F) - closed cup
Boiling Point · 6건

221 °F at 760 mmHg (USCG, 1999)

106.0 °C

106 °C

223 °F

106 °C @760 [mm Hg]

223 °F

Decomposition · 4건

Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gas.

When heated to decomposition it emits toxic fumes of /chloride/.

Not combustible, but if involved in a fire decomposes to produce hydrogen chloride.

Decomposes in water to form chloroacetic acid and hydrogen chloride gas.

Melting Point · 6건

-8.5 °F (USCG, 1999)

-21.7 °C

-21.8 °C

-8.5 °F

-22 °C

-7 °F

Vapor DensityRelative vapor density (air = 1): 3.9

물리화학적 성질

녹는점
22 °C · −22 °C(lit.)
끓는 점
105 · 105-106 °C(lit.)
밀도
1.419 g/mL · 1.419 g/mL at 20 °C
증기 밀도
3.9 · 3.9 (vs air)
증기압
60 mm · 60 mm Hg ( 41.5 °C)
굴절률
20 · n20/D 1.453(lit.)
인화점
100 °C · >100°C
저장 조건
Store at RT.
용해도
에틸 에테르, 아세톤, 벤젠 및 사염화탄소와 혼합 가능합니다.
물리적 상태
액체
색상
무색투명~미황색
냄새
강한 자극적인 냄새
수용성
물과 반응
Merck
14 · 14,2067
BRN
605439 · 605439
Henry's Law Constant
2.9 · 2.9×10-1 mol/(m3Pa) at 25℃, Wang et al. (2017)
안정성
안정적인. 강염기, 알코올, 강산화제와 호환되지 않습니다. 물이나 습기에 노출되면 격렬하게 반응할 수 있습니다.
InChI
1S/C2H2Cl2O/c3-1-2(4)5/h1H2
InChIKey
VGCXGMAHQTYDJK-UHFFFAOYSA-N
SMILES
ClCC(=O)Cl
NIST
Acetyl chloride, chloro-(79-04-9)
EPA
Chloroacetyl chloride (79-04-9)

화학적 성질

Chloroacetyl chloride is a colorless to yellowish liquid with a very pungent, extremely irritating, odor.

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNot combustible, but if involved in a fire decomposes to produce hydrogen chloride.
Health Hazards · 2건

Inhalation causes severe irritation of upper respiratory system. External contact causes severe irritation of eyes and skin. Ingestion causes severe irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1건

Liquid causes second or third degree burns after short contact; [CHRIS] Corrosive to skin; [Quick CPC] Hydrolysis of chloroacetyl chloride yields chloroacetic acid and hydrogen chloride gas. It causes clinical and pathologic evidence of respiratory effects at the lowest concentrations tested in experimental animals; [ACGIH] A lachrymator; [HSDB]

DOT ID and Guide · 2건

1752 156

1752 156

Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: T, C, N; R: 14-23/24/25-35-48/23-50; S: (1/2)-7/8-9-26-36/37/39-45-61
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 8; UN Pack Group: I
Reactivity AlertsWater-Reactive

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Give nothing to drink. Refer for medical attention .

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3건

Excerpt from NIOSH Pocket Guide for Chloroacetyl chloride:

General First Aid:

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Dry. Keep in a well-ventilated room.
Exposure Control and Personal Protection · 2건

· Wear positive pressure self-contained breathing apparatus (SCBA).

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 · 5건

Suitable extinguishing media: Dry powder, dry sand. Unsuitable extinguishing media: Do NOT use water jet.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray to keep fire-exposed containers cool. Extinguish fire using agent suitable for surrounding fire.

If material involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Storage Conditions · 3건

Store under nitrogen. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Keep away from water. Never allow product to get in contact with water during storage. Hydrolyzes readily.

Store in a cool, dry, well-ventilated location. Separate from combustibles, alkalies, alcohols.

Protect from moisture.

Cleanup Methods · 2건

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Do not flush with water. Keep in suitable, closed containers for disposal.

Approach release from upwind. Keep water away from release. Stop or control the leak, if this can be done without undue risk. Prompt cleanup and removal is necessary. Control runoff and isolate discharged material for proper disposal.

Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Disposal Methods · 3건

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.

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.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Spillage Disposal · 1건

Cover the spilled material with dry sand. Collect leaking and spilled liquid in sealable containers as far as possible. Then store and dispose of according to local regulations. NEVER direct water jet on liquid. Personal protection: complete protective clothing including self-contained breathing apparatus.

독성 정보

Target OrgansEyes, skin, respiratory system
Environmental Fate · 3건

TERRESTRIAL FATE: Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, adsorption, volatilization and biodegradation are not expected to be important fate processes in moist soil(SRC). Chloroacetyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 25.2 mm Hg at 25 °C(2).

AQUATIC FATE: Chloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, adsorption to suspended solids and sediment, bioconcentration, volatilization, and biodegradation are not expected to be important fate processes in aquatic systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetyl chloride, which has a vapor pressure of 25.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroacetyl chloride 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 670 days(SRC), calculated from its rate constant of 2.4X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Chloroacetyl chloride contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation of its aerosol or vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Toxicity Summary · 1건

IDENTIFICATION AND USE: Chloroacetyl chloride is a liquid. It is used in the synthesis of organic compounds. It is also used as a tear gas. HUMAN STUDIES: The effects of acute exposure include: skin erythema and burns, respiratory effects including dyspnea, cyanosis, and cough, and gastrointestinal effects. Painful eye irritation and lacrimation around 1 ppm. Chloroacetyl chloride may promote ventricular arrhythmias. ANIMAL STUDIES: A subchronic inhalation study was conducted in which rats, mice, and hamsters were exposed at averaged vapor concentrations of 0, 0.5, 1, 2.5, or 5 ppm chloroacetyl chloride 6 hours/day, 5 days/week for 4 weeks. Most of the rats inhaling the 5 ppm or 2.5 ppm concentrations died during the first 2 weeks of exposure. Mortality in mice at these two higher concentrations was 15% and 10%, respectively. All animals survived in the other exposure groups, including hamsters at all concentrations. Respiratory and/or eye irritation was observed in all three species at all exposure levels. Chloroacetyl chloride was not mutagenic in five strains of Salmonella, with or without metabolic activation. It did not induce sister chromatid exchange or chromosomal aberrations in Chinese hamster cells when tested both with and without metabolic activation.

Signs and Symptoms · 5건

Cough. Laboured breathing. Burning sensation. Blue lips, fingernails and skin. Shortness of breath. Sore throat. Symptoms may be delayed.

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

Pain. Redness. Blurred vision. Severe deep burns.

Burning sensation. Abdominal pain. Diarrhoea. Shock or collapse.

irritation eyes, skin, respiratory system; eye, skin burns; cough, wheezing, dyspnea (breathing difficulty); lacrimation (discharge of tears)

Ongoing Test Status · 1건

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of March 27, 2018: http://actor.epa.gov/dashboard/]

Soil Adsorption/MobilityChloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, adsorption to soil and leaching are not expected to be important fate processes(SRC).
TSCA Test Submissions · 5건

Chloroacetyl chloride (CAS # 79-04-9) was evaluated for acute oral toxicity in Sprague-Dawley albino rats (alternately 2 male and 3 female and 3 male and 2 female/group) administered single doses of 126, 158, 200, and 251 mg/kg by oral gavage. Treatment was associated with toxic signs including weakness, collapse, diminished weight gain among high-dose study survivors, and death consistent with an oral LD50 in rats of 207 (187-229) mg/kg. Gross necropsy of the study lethalities found hemorrhagic lungs and liver and gastrointestinal inflammation; the study survivors, necropsied 9 days after dosing, exhibited focal lung congestion, slight discoloration of the liver, and slight gastrointestinal inflammation.

Chloroacetyl chloride (CAS # 79-04-9) was evaluated for acute dermal toxicity in male and/or female New England white rabbits administered single applications of undiluted doses at 0.2 incremental fractional log intervals (126, 200, 316, 501, 794, 1,260, 2,000, 5,010, and 10,000 mg/kg) upon clipped intact skin. Application sites were covered with semi-occluded dressings while animals were restrained in stocks to prevent anything but a dermal exposure, the dressing and test substance removed after 24 hours. Treatment was associated with signs of systemic toxicity including reduced appetite of 3-5 days' duration in study survivors, progressive weakness, dyspnea, collapse, and death consistent with a minimal lethal dose between 316 and 501 mg/kg, and with time to death (3 hours - 2 days) inversely correlated to dose. Upon necropsy of study lethalities, visceral abnormalities included slightly enlarged gall bladder and hemorrhagic lungs and liver. The study survivors exhibited no treatment-related gross pathology upon Day 14 post-treatment sacrifice, other than the severe deep dermal injury which was common in all treated rabbits.

Chloroacetyl chloride (CAS # 79-04-9) was evaluated for acute inhalation toxicity in 4 mature male rats administered a single exposure to a dynamically-generated concentrated atmosphere (27.9 g vaporized and supplied at 4/L min to a 35 L environmental chamber) for 2 hours. The atmosphere proved to be extremely toxic, the animals exhibiting immediate irritative responses including pawing at face and mouth with eyes tightly shut, reddened eyes with nasal and salivary excretion (2 min), erratic respiration (2 min), gasping and grogginess (10 min), damp fur (20 min), opaque cornea and blindness (30 min), weakness nearing collapse (60 min), and death (3/4 at 90 min; 1/4 at 120 min). Gross necropsy revealed acutely hemorrhagic lungs.

Chloroacetyl chloride (CAS # 79-04-9) was evaluated for primary dermal irritation in male and/or female New England white rabbits administered single undiluted applications at doses of 0.2 fractional log increments upon clipped intact skin for 24 hours. Each application site was covered with a plastic dressing to retard evaporation and contamination. Chloroacetyl chloride proved a corrosive dermal irritant to rabbits under the conditions of this study, causing an average maximum irritation score (Draize, Woodard, and Calvery) of 6.0 of a possible 8.0 within 2 hours and unanimous deep dermal injury by end of study.

Human Toxicity Excerpts · 3건

/SIGNS AND SYMPTOMS/ Medical reports of the effects of acute exposure include: skin erythema and burns; respiratory effects including dyspnea, cyanosis, and cough; and gastrointestinal effects.

/SIGNS AND SYMPTOMS/ ... No eye irritation at 0.140 ppm but ... painful eye irritation and lacrimation around 1 ppm.

/CASE REPORTS/ A male employee of a pharmaceutical company experienced a large skin area exposure to a mixture of chloroacetyl chloride, xylidine, and benzene. The worker was put under a shower within 5 min of the accident, but shortly thereafter, he began to have respiratory difficulties, collapsed, and experienced an apparent grand mal seizure. At the time of the published account, 2 years after the accident, the patient was still comatose. The relative contribution of the three chemicals to the patient's condition is unknown. However, the authors related information obtained from the chloroacetyl chloride manufacturer that two fatalities had resulted from exposure to chloroacetyl chloride, one of them following massive skin contact followed by cardiorespiratory arrest within a few minutes. According to that manufacturer, other data indicated that chloroacetyl chloride may promote ventricular arrhythmias.

Artificial Pollution Sources · 1건

Chloroacetyl chloride's production and use as a reactive intermediate in the manufacture of adrenalin, diazepam, chloroacetophenone, chloroacetate esters, chloroacetic anhydride, tear gas agents and herbicides, such as alachlor(1,2) may result in its release to the environment through various waste streams(SRC).

Environmental BioconcentrationChloroacetyl chloride reacts rapidly with water forming chloroacetic acid and hydrochloric acid(1). As a result, bioconcentration is not expected to be an important fate process(SRC).

규제 정보

DHS Chemicals of Interest (COI) · 4건

Chloroacetyl chloride

A Commercial Grade

A Placarded Amount

Chemical or material that can be mixed with readily available materials.

안전 데이터

OEB
C
OEL
TWA: 0.05 ppm (0.2 mg/m3)
wgk
3
IDLA
1.3 ppm (6 mg/m3)
tsca
TSCA listed
rtecs
AO6475000
ridadr
UN 1752
HS 번호
29159000
risk_code
14-23/24/25-35-48/23-50-29
hazard_code
T,C,N
safety_code
9-26-36/37/39-45-61-7/8
포장분류
I
위험 등급
6.1
기존화학 물질
KE-05500
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Eye Dam. 1Skin Corr. 1ASTOT RE 1
스토리지 클래스
6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
79-04-9(Hazardous Substances Data)
Intermediate
Methods of Manufacturing · 4건

Chloroacetyl chloride is usually manufactured from chloroacetic acid by reaction with phosphorus trichloride, thionyl chloride, sulfuryl chloride, or phosgene. It is also obtained by chlorination of acetyl chloride in the presence of stronger aliphatic acids, preferably chloroacetic acids, or from sodium chloroacetate and the usual chlorinating agents.

Manufactured by reaction of chloroacetic acid with chlorinating agents such as phosphorus oxychloride, phosphorus trichloride, sulfuryl chloride or phosgene. Various catalysts have been used to promote the reaction. Chloroacetyl chloride is also produced by chlorination of acetyl chloride, the oxidation of 1,1-dichloroethene, and the addition of chlorine to ketene..

Preparation from chloroacetic acid and benzoyl chloride ... ; by chlorination of ketene ... ; Prill, United States patent 2889365 (1959 to Monsanto); from chloroacetic acid and pyrocatechylphosphorus trichloride ... . Manufactured from chloroacetic acid and POCl2: MacKenzie, Morris, United States patent 2848491 (1958 to Dow); from ketene: Prill, United States patent 2889365 (1959 to Monsanto).

(1) Action of chlorine on acetyl chloride in sunlight. (2) Dropping phosphorus trichloride on chloroacetic acid.

General Manufacturing Information · 3건

All Other Basic Organic Chemical Manufacturing

Acetyl chloride, 2-chloro-: ACTIVE

Chloroacetyl chloride is usually manufactured from chloroacetic acid by reaction with phosphorus trichloride, thionyl chloride, sulfuryl chloride, or phosgene. It is also obtained by chlorination of acetyl chloride in the presence of stronger aliphatic acids, preferably chloroacetic acids, or from sodium chloroacetate and the usual chlorinating agents.

응용 분야

용도Chloroacetyl chloride is an intermediate in the production of alachlor and butachlor. It is used to prepare phenacyl chloride through Friedel-Crafts acylation of benzene.

일반 설명A colorless to light yellow liquid with a very pungent odor. Very toxic by inhalation. Corrosive to metals and tissue.

제조 방법 · 1건

Chloroacetyl chloride is usually manufactured from chloroacetic acid by reaction with phosphorus trichloride, thionyl chloride, sulfuryl chloride, or phosgene. It is also obtained by chlorination of acetyl chloride in the presence of stronger aliphatic acids, preferably chloroacetic acids, or from sodium chloroacetate and the usual chlorinating agents.Koenig G et al; Chloroacetic Acids. Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2018). NY, NY: John Wiley & Sons. Online Posting Date: October 15, 2012

상·하류 제품 정보

상류 원료

아세틸 케텐유황클로로아세트산염소(기체)염화 아연이황화몰리브덴클로로술폰산포스겐이염화유황염화벤조일메탄

하류 제품

4-(아세틸아미노)페닐클로로아세테이트2-Chloro-N-(2,6-dimethylphenyl)acetamideD-Serine5-Methylthianaphthene에틸1-(2-클로로아세틸)-4-피페리딘카복실레이트2-Chloro-N,N-dimethylacetamidePropacetamol7-chloro-1,3-dihydro-5-phenyl-2-oxo-2H-1,4-benzodiazepin-3-yl acetateBenzyl 2-chloroacetate2-AMINO-3-CYANO-4-CHLORO-5-FORMYLTHIOPHENED-Threonine리도카인 수화염화물CHLOROMETHYLACETAMIDE프레틸라클로데목세팜2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL디클로페낙 나트륨N-메틸-N-페닐-2-피페라진-1-일라세타미드FLURAZEPAM메톨라클로르아닐로포스Azasetron hydrochlorideD-Tyrosine보네코르클로로아세트산터셔리부틸에스테르6-클로로-2-(클로로에틸)-3-옥시도-4-페닐-퀴나졸린N-(2-벤조일-4-니트로페닐)-2-클로로아세트아미드PraziquantelNitrazepamPirenzepine모르포티온에멀젼리도카인Estazolam다이아제팜CHLOROTRIANISENEa-클로로아세토페논로라제팜6-NITRO-2H-1,4-BENZOXAZIN-3(4H)-ONE2,2',4'-TrichloroacetophenonePropachlor

추가 설명

정의Chloroacetyl chloride is classified as an acyl halide. It is a colorless to light yellow liquid with a strong, pungent odor. This compound is highly toxic when inhaled and can corrode both metal surfaces and tissues.

For more TSCA Test Submissions (Complete) data for Chloroacetyl chloride (9 total), please visit the HSDB record page.