Acetyl chloride

HCID 6367CAS 75-36-5

Basic information

Standard SMILES
CC(=O)Cl
InChIKey
WETWJCDKMRHUPV-UHFFFAOYSA-N
Molecular formula
C2H3ClO
Average molar mass
78.5 g/mol
Monoisotopic mass
77.9872424

Names & identifiers

Preferred name
Acetyl chloride
IUPAC
acetyl chloride
English name
Acetyl chloride
Molecular formula
C2H3ClO
Molecular weight
78.5

Names & synonyms

ACETYL CHLORIDE75-36-5Ethanoyl chlorideAcetic chlorideAcetic acid chlorideAcetylchlorideAcetic acid, chlorideQD15RNO45KDTXSID2023852CHEBI:37580RefChem:5510DTXCID203852
Show more names
AcClLidocaine Impurity 38ACETYL-TRANS-RESVERATROLACETYLCLORIDEAcetylchloridUN1717 (DOT)
200-865-6CH3COClRCRA waste number U006CH3-CO-ClMFCD00000719C2H3ClOAcetyl chloride, reagent grade, 98%CCRIS 4568

Database identifiers

CAS
75-36-5
PubChem CID
6367
DTXSID
DTXSID2023852
ChEBI
CHEBI:37580
UNII
QD15RNO45K
EC Number
200-865-6
Nikkaji
J1.453B

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
4

Experimental & physicochemical properties

LogP-0.47
Odor · 2 items

Pungent odor

Sharp odor

Density · 6 items

1.1039 at 69.8 °F (USCG, 1999) - Denser than water; will sink

1.1051g/cu cm at 20 °C

Saturated liquid density: 68.849 Lb/cu ft at 70 °F

Saturated vapor density: 0.06130 Lb/cu ft at 70 °F

Relative density (water = 1): 1.11

1.1051 @ 20°C

Color/Form · 2 items

Liquid

Colorless fuming liquid

Solubility · 6 items

Reaction (NTP, 1992)

Decomposed violently by water or alcohol

Miscible with benzene, chloroform, ether, glacial acetic acid, petroleum ether

Miscible with ether, acetone, benzene, chloroform; soluble in carbon tetrachloride

Soluble in ether, acetone, acetic acid

Solubility in water: reaction

Corrosivity · 2 items

Corrosive

Corrosive to metals and tissue

Physicochemical properties

Melting point
-112 °C · -112 °C
Boiling point
52 °C · 52 °C(lit.)
Density
1.104 g/mL · 1.104 g/mL at 25 °C(lit.)
vapor density
2.7 · 2.7 (vs air)
vapor pressure
11.69 psi · 11.69 psi ( 20 °C)
refractive index
20 · n20/D 1.389(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids];H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Hazards IdentificationWater-reactive material (WR)
Regulatory Information · 5 items

Chemical: Acetyl chloride

Acetyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetyl chloride 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: 02-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13323

Acetyl chloride: HSNO Approval: HSR001073 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 LabelFlammable Liquid Corrosive
Fire Hazards · 3 items

Special Hazards of Combustion Products: When heated to decomposition, hydrogen chloride and phosgene, extremely poisonous gases, are evolved.;Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapors may travel to source of ignition and flash back.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff.;· Corrosives in contact with metals may evolve flammable hydrogen gas.;· Containers may explode when heated or if contaminated with water.

Highly flammable. Many reactions may cause fire or explosion. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 2 items

Dangerous fire hazard when exposed to heat or flame.

Flammable.

Health Hazards · 2 items

Vapor irritates mucous membranes. Ingestion of liquid or contact with eyes or skin causes severe irritation. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.;· Bromoacetates and chloroacetates are extremely irritating/lachrymators (cause eye irritation and flow of tears).;· Reaction with water or moist air may release toxic, corrosive or flammable gases.;· Reaction with water may generate much heat that will increase the concentration of fumes in the air.;· Fire will produce irritating, corrosive and/or toxic gases.;· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:;Note: Most foams will react with the material and release corrosive/toxic gases. CAUTION: For Acetyl chloride (UN1717), use CO2 or dry chemical only.;SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam.;LARGE FIRE: Water spray, fog or alcohol-resistant foam. FOR CHLOROSILANES, DO NOT USE WATER; use alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Avoid aiming straight or solid streams directly onto the product.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use powder, carbon dioxide. NO hydrous agents, water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4 items

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

Wear protective gloves when administering first aid. First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

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

Accidental Release Measures · 2 items

· 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.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.;· Stop leak if you can do it without risk.;· A vapor-suppressing foam may be used to reduce vapors.;· FOR CHLOROSILANES, use alcohol-resistant foam to reduce vapors.;· DO NOT GET WATER on spilled substance or inside containers.;· Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material.;· Prevent entry into waterways, sewers, basements or confined areas.;Small Spill;· Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain.;· Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.

First Aid · 2 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

Safe StorageFireproof. Store in an area without drain or sewer access. Separated from incompatible materials. See Chemical Dangers. Dry. Well closed.
Firefighting HazardsVarpors are heavier than air and may travel to a source of ignition and flash back. ... Closed containers may rupture violently when heated.

Toxicology

Ecotoxicity ValuesLC50; Species: Pimephales promelas (Fathead minnow); Conditions: freshwater, static; Concentration: 42 mg/L for 96 hr (95% confidence interval: 25.2-70 mg/L)
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that acetyl chloride is expected to have very high mobility in soil(SRC). In view of its violent decomposition in the presence of water(3) and the high reactivity of structurally-similar compounds with active hydrogen groups that occur in soil(4), it is unlikely that acetyl chloride would persist for long in moist soils(SRC). Acetyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 287 mm Hg at 25 °C(5). Biodegradation data in soil were not available(SRC, 2018).

AQUATIC FATE: Acetyl chloride decomposes violently in the presence of water(1) and, therefore, will not persist in the aquatic environment(SRC). Adsorption to sediment, volatilization, bioconcentration in aquatic species or biodegradation are not expected because of the very short lifetime of this compound in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetyl chloride, which has a vapor pressure of 287 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetyl chloride may be 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 years(SRC), calculated from its rate constant of 9.1X10-15 cu cm/molecule-sec at 25 °C(3). However, acetyl chloride decomposes violently in the presence of water(4) and fumes in the presence of moist air(5). Acetyl chloride contains chromophores that absorb at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Exposure RoutesSerious local effects by all routes of exposure.
Toxicity Summary · 1 item

IDENTIFICATION AND USE: Acetyl chloride is a colorless fuming liquid. It is used as an acetylating agent, reagent in testing for cholesterol, and for determination of water in organic liquids. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: In the Ames test using Salmonella culture strains TA97 TA100 TA1535 TA1537 acetyl chloride was not mutagenic with or without exogenous metabolic activation. Genotoxic activity of acetyl chloride was investigated in both somatic and germ cells of Drosophila melanogaster. Only marginal genotoxic activities were observed in these cells.

Signs and Symptoms · 4 items

Cough. Sore throat. Burning sensation. Shortness of breath.

Redness. Pain. Burning sensation. Blisters. Serious skin burns.

Redness. Pain. Severe burns.

Cough. Sore throat. Burning sensation behind the breastbone. Abdominal pain. Shortness of breath.

Regulatory information

Regulatory Information · 5 items

Chemical: Acetyl chloride

Acetyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetyl chloride 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: 02-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13323

Acetyl chloride: HSNO Approval: HSR001073 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.)

RCRA Requirements · 1 item

U006; As stipulated in 40 CFR 261.33, when acetyl chloride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Acetyl chloride is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 1 item

Acetyl chloride is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

DHS Chemicals of Interest (COI) · 4 items

Acetyl chloride

A Commercial Grade

A Placarded Amount

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

Safety data

F
3
wgk
1
tsca
TSCA listed
rtecs
AO6390000
ridadr
UN 1717
hs_code
29159080

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used in chemical production and assays; [HSDB]

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

Acetylating agent; in testing for cholesterol, determination of water in organic liquids.

Organic preparations (acetylating agent); dyestuffs; pharmaceuticals.

Acetyl chloride is an efficient acetylating agent for alcohols and amines to produce esters and amides. It is important in the synthesis of dyes and pharmaceuticals. Acetyl chloride is used in the Friedel-Craft acylation of benzene to yield acetophenone.

Acetyl chloride is a powerful acetylating agent. It is used in the manufacture of aspirin, acetaminophen, acetanilide, and acetophenone. Liquid crystal compositions for optical display and memory devices frequently require acetyl chloride.

ImpuritiesAcetyl chloride frequently contains 1-2% by weight of acetic acid or hydrochloric acid. Phosphorus or sulfur-containing acids may also be present in the commercial material.
U.S. Production · 5 items

2023: 50,000 - <250,000 lb;2022: <50,000 lb;2021: <50,000 lb;2020: <50,000 lb

(1972) LESS THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

The total U.S. market may amount to only 500 metric ton annually.

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Acetyl chloride:;Table: National Aggregate Production Volume (pounds) [Table#1916]

Consumer UsesIntermediate
Industry UsesIntermediate
Methods of Manufacturing · 5 items

Prepared from acetic acid and chlorine in the presence of phosphorus; from acetic acid and salts of chlorosulfonic acid; from sodium acetate and sulfuryl chloride. ... Lab preparation from acetic anhydride and calcium chloride.

By mixing glacial acetic acid and phosphorus trichloride in the cold and heating a short time to drive off hydrochloric acid. The acetyl chloride is then distilled.

The normal industrial method involves reaction of acetic anhydride with anhydrous hydrogen chloride. On the laboratory scale, it can be produced from acetic acid and reagents such as thionyl chloride, phosphorus trichloride, or phosphorus pentachloride.

Acetyl chloride was formerly manufactured by the action of thionyl chloride, Cl2OS, on gray acetate of lime, but this route has been largely supplanted by the reaction of sodium acetate or acetic acid and phosphorus trichloride.

Other acetyl chloride preparations include: the reaction of acetic acid and chlorinated ethylenes in the presence of ferric chloride; a combination of benzyl chloride and acetic acid at 85% yield; conversion of ethylidene dichloride, in 91% yield; and decomposition of ethyl acetate by the action of phosgene ... .

Applications · 7 items

UsesAcetyl Chloride is a very useful synthetic intermediate. It is a derivative of acetic acid, a weak acid, used as a reagent in numerous industrial processes. It is a chemical for acetylation in the synthesis or derivatization of organic compounds.

Uses1. It is a kind of acetylating agent, being used as raw materials for pesticides and medicine, or the intermediates for the manufacturing of water treatment agent ethylidene diphosphate. 2. It can be used for the analysis of reagents as well as used for the preparation of acetyl derivatives and dyes 3. It can be used for organic synthesis, dyes and pharmaceutical industries 4. It can be used as the raw materials of pesticides and pharmaceutical as well as the intermediate for the manufacture of water treatment agent ethylene diphosphate. Moreover, it can also be used for the manufacture of new electroplating complexing agent. Acetyl chloride is an important acetylating agent with the acylation capability being stronger than acetic anhydride. It is widely used in organic synthesis and dyes. It is also the catalyst for the carboxylic acid to have chlorination reaction as well as being used for hydroxyl and amino quantitative analysis. 5. This product can be used as raw material for organic synthesis, used in the production of pesticides, pharmaceuticals, new electroplating complexing agent, the catalyst for carboxylic acid to have chlorination, acetylation agent, and other kinds of fine organic synthesis intermediates.

DescriptionAcetic chloride is a colourless to light yellow liquid with a pungent and choking odour. Acetic chloride is highly flammable and reacts violently with DMSO, water, lower alcohols, and amines to generate toxic fumes. Along with air, acetic chloride may form an explosive mixture. It is incompatible with water, alcohols, amines, strong bases, strong oxidising agents, and most common metals. On decomposition when heated, acetic chloride produces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.

UsesAcetyl chloride acts as a reagent for the preparation of esters and amides of acetic acid. It is also useful an important reactant in Friedel-Crafts reactions as well as the introduction of an acetyl group. It serves as a starting material in the production of pharmaceutical, new plating complexing agent, acylation agent and synthetic organic intermediates.

UsesAcetyl chloride can be used as: A degradation agent in the degradation of polyoxyethylene glycol monoalkyl ethers to determine the degree of ethoxylation using chromatography-mass spectrometry (MS). A reagent with alcohols for the esterification of carboxylic acids, N-boc deprotection, and phosphoramide solvolysis reactions.

UsesAcetylating agent; in testing for cholesterol, determination of H2O in organic liquids.

General DescriptionA colorless, fuming liquid with a pungent odor. Density 9.2 lb / gal. Flash point 40°F. Vapor, which is heavier than air, irritates the eyes and mucous membranes. Corrosive to metals and tissue. Acetyl chloride, CH30CCI, can be prepared by treatment ofacetic acid with various reagents, such as PCl3 SOCl2 or COCI2. It can be prepared by chlorination of acetic anhydride in several different ways, by reaction of methyl chloride with carbon monoxide in the presence of catalysts, by reaction ofketene with HCI, or by partial hydrolysis of 1, 1, l-trichloroethane, Acetyl chloride hydrolyzes in the presence of water to give acetic acid. It reacts with ammonia and amines to give acetamides. Reaction with alcohols gives the corresponding acetate esters. Acetyl chloride will add across unsaturated bonds in the presence ofsuitable catalysts to give halogenated ketones.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Additional notes

DefinitionA liquid acyl chloride used as an acetylating agent.

Related reactions

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Linked notes

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