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75-36-5

75-36-5 Structure

75-36-5 Structure
IdentificationMore
[Name]

Acetyl chloride
[CAS]

75-36-5
[Synonyms]

acetic acid chloride
Acetic chloride
ACETYL CHLORIDE
AKOS BBS-00003929
ETHANOIC ACID CHLORIDE
ETHANOYL CHLORIDE
Acetic acid monochloride
Acetylchlorid
acetylchloride313
CH3COCl
Ethanoylcholride
Rcra waste number U006
rcrawastenumberu006
UN1717 (DOT)
Acetyl chloride? Ethanoyl chloride
ACETYL CHLORIDE 98% MIN.
Acetyl chloride 99+ % for analysis
Acetyl chloride
Acetyl chloride 99+ % for analysis
ACETYL CHLORIDE, REAGENTPLUS, >=99% ACETYL CHLORIDE, REAGENTPLUS, >=99%
ACETYL CHLORIDE REAGENT GRADE 98%
[EINECS(EC#)]

200-865-6
[Molecular Formula]

C2H3ClO
[MDL Number]

MFCD00000719
[Molecular Weight]

78.5
[MOL File]

75-36-5.mol
Chemical PropertiesBack Directory
[Description]

Acetic 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.
[Appearance]

Acetyl chloride is a highly flammable, colorless, fuming liquid with a pungent odor
[Appearance]

colourless to light yellow liquid with a pungent
[mp ]

-112 °C
[bp ]

52 °C(lit.)
[density ]

1.104 g/mL at 25 °C(lit.)
[vapor density ]

2.7 (vs air)
[vapor pressure ]

11.69 psi ( 20 °C)
[refractive index ]

n20/D 1.389(lit.)
[Fp ]

40 °F
[storage temp. ]

Store at RT
[Stability:]

Stability Highly flammable. Reacts violently with DMSO, water, lower alcohols, and amines to generate toxic fumes. May form an explosive mixture with air. Note low flash point. Incompatible with water, alcohols, amines, strong bases, strong oxidizing agents, most common metals.
[Sensitive ]

Moisture Sensitive
[Merck ]

14,85
[BRN ]

605303
[CAS DataBase Reference]

75-36-5(CAS DataBase Reference)
[NIST Chemistry Reference]

Acetyl chloride(75-36-5)
[EPA Substance Registry System]

75-36-5(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

Acetic chloride is a colorless to light yellow liquid with a pungent and choking odor. Acetic chloride is highly flammable, reacts violently with dimethyl sulfoxide (DMSO), water, lower alcohols, and amines to generate toxic fumes. Together with air, acetic chloride may form an explosive mixture. It is incompatible with water, alcohols, amines, strong bases, strong oxidizing agents, and most common metals. On decomposition when heated, acetic chloride produces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.
[General Description]

A 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 .
[Reactivity Profile]

ACETYL CHLORIDE reacts violently with water, steam, methanol or ethanol to form hydrogen chloride and acetic acid. Reacts vigorously with bases, both organic and inorganic. Incompatible with oxidizing agents and alcohols. Produces highly toxic fumes of phosgene gas and chlorine when heated to decomposition [Sax, 9th ed., 1996, p. 35]. Reaction in a confined space with even a small amount of water may cause a violent eruption of gases [Bretherick, 5th ed., 1995, p. 281]. Vapor forms an explosive mixture with air [Kirk-Othmer, 3rd ed., Vol. 1, 1978, p. 162]. Polymerization reaction with dimethyl sulfoxide is particularly violent [Buckley, A., J. Chem. Ed., 1965, 42, p. 674]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
[Health Hazard]

Exposure to acetic chloride causes severe health effects. It is corrosive and causes severe skin burns. On contact with the eyes and skin and accidental ingestion, acetic chloride causes permanent eye damage and serious burns to the mouth and stomach. The spray mist or liquid causes tissue damage (mucous membranes of eyes, mouth, and upper respiratory tract). Inhalation of the spray mist causes severe irritation of the respiratory tract, with symptoms of a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Prolonged periods of inhalation of acetic chloride may be fatal as a result of spasm, infl ammation, and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema characterized by coughing, choking, or shortness of breath. However, there is no published information about the carcinogenicity, mutagenicity, teratogenicity, and developmental toxicity of acetic chloride in animals and humans.
[Health Hazard]

Vapor irritates mucous membranes. Ingestion of liquid or contact with eyes or skin causes severe irritation.
[Potential Exposure]

Acetyl chloride is used in organic synthesis as an acetylating agent and in testing for water and/ or cholesterol in organic liquids, in the pharmaceutical industry and in pesticide manufacture.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once, and irrigate immediately for at least 30 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Do not induce vomiting. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed
[Shipping]

UN1717 Acetyl chloride, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material
[Incompatibilities]

ticide manufacture. Incompatibilities: Avoid contact with moisture, steam, water, alcohols, dimethylsulfoxide, strong bases; phosphorus trichloride; oxidizers, and amines, since violent reactions may occur. Keep away from heat, fire, and welding operations.
[Waste Disposal]

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. May be mixed slowly with sodium bicarbonate solution and then flushed to sewer with large volumes of water. May also be incinerated.
Safety DataBack Directory
[Hazard Codes ]

F,C
[Risk Statements ]

R11:Highly Flammable.
R14:Reacts violently with water.
R34:Causes burns.
[Safety Statements ]

S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S1/2:Keep locked up and out of the reach of children .
[RIDADR ]

UN 1717 3/PG 2
[WGK Germany ]

1
[RTECS ]

AO6390000
[F ]

3
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29159080
[storage]

Acetic chloride should be stored in a segregated and approved area, away from incompatibles such as oxidizing agents, alkalis and moisture. The container of acetic chloride should be kept in a cool, well-ventilated area, tightly sealed until ready for use. Users should avoid all possible sources of ignition, i.e., spark or flames.
[Safety Profile]

Poison by inhalation. Moderately toxic by ingestion. A human systemic irritant by inhalation. Violent hydrolysis reaction with water or steam produces heat, acetic acid, HCl, and other corrosive chlorides. May decompose during preparation. Dangerous fire hazard when exposed to heat or flame. Explosion hazard by spontaneous chemical reaction with dimethyl sulfoxide or ethanol. Also incompatible with Pcb. When heated to decomposition it emits highly toxic fumes of phosgene and Cl-. To fight fire, use CO2 or dry chemical. See also CHLORIDES
[Hazardous Substances Data]

75-36-5(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Acetic acid glacial-->Carbon tetrachloride-->Phosphorus trichloride-->Sodium acetate-->Phosphorus pentachloride-->Sulfur dioxide-->PHOSGENE-->Tetrachlorosilane-->DOYLE DIRHODIUM CATALYST-RH2(4S-MEOX)4
[Preparation Products]

2-MERCAPTO-6-METHYLPYRIMIDIN-4-OL-->4-BROMO-2-CHLOROACETANILIDE-->4-BROMO-3-CHLOROACETANILIDE-->5-AMINO-3-METHYL-ISOXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->1,4-Naphthalenedicarboxylic acid-->4'-BROMO-2'-METHYLACETANILIDE-->1-PYRENECARBOXYLIC ACID-->2-ACETYL-3-BROMOTHIOPHENE-->2-Acetoxy-2-phenylacetyl chloride-->finishing agent for wool baylan W-G3-->Acetazolamide-->2,2,2-Trichloro-1-phenylethyl acetate-->2-ACETYL-3-CHLOROTHIOPHENE-->1-(2-Hydroxy-5-methylphenyl)ethanone-->5-ACETAMIDONAPHTHALENE-1-SULFONYL CHLORIDE-->2',4'-Dichloroacetophenone-->1,1,1-TRICHLOROACETONE-->Acetylcholine chloride-->5-ACETYL-2,3-DIHYDROBENZO(B)FURAN-->2-Methyl-2-thiazoline-->4-Acetylbiphenyl-->ETHYL 3-(4-ISOBUTYLPHENYL)-3-METHYL GLYCIDATE-->4-(4-CHLOROPHENOXY)-2 CHLORO PHENYL ETHANONE-->4'-(Trifluoromethoxy)acetophenone-->4,4'-Diacetylbiphenyl-->2-(2-Butoxyethoxy)ethyl acetate-->3-Acetylthianaphthene-->3-Chloro-4-fluoroacetophenone-->Acetoxyacetyl chloride-->1-(2,4-DICHLORO-3-METHYLPHENYL)ETHANONE-->5-Acetylsalicylamide-->Acetyltropylic chloride-->2-ACETYL-5-CHLOROTHIOPHENE-->1,1'-Diacetylferrocene-->N-ACETYLTHIOUREA-->1,4-Butane sultone-->Formyl acetate-->N,N-DI-N-BUTYLACETAMIDE-->2-HYDROXY-N-METHYL-N-PHENYL-ACETAMIDE-->PYRUVONITRILE
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Acetic acid chloride(75-36-5).msds
Questions And AnswerBack Directory
[Physical and chemical properties]

It appears as colorless fuming liquid with a strong odor and eye irritation effect. The relative density of 1.1051 (20 ° C), the melting point of-112 ° C, the boiling point of 51-52 ° C and the flash point is 4.4 ° C (closed dish). In the wet air, it can slowly undergo decomposition and give white smoke. When coming across water, it can be violently hydrolyzed into acetic acid and hydrogen chloride, and thus should be sealed for storage. It is miscible with benzene, acetone, chloroform, ether, glacial acetic acid and petroleum ether. Liquid is heavier than water with the vapor being heavier than air. Its chemical nature is lively. It can have metathesis reaction with many compounds. Acetyl chloride can bind to the thiol group in the protein, and therefore being toxic to humans. It is an important kind of acetylation agents with its acylation capability being stronger than acetic anhydride. It is widely used in organic synthesis, being also the catalyst for the chlorination of carboxylic acids. It is manufactured through the mixing of glacial acetic acid and phosphorus trichloride in cold condition with further heating, followed by dehydrochloration distillation.
[Dangerous situation]

(1) It has corrosive effect against the skin and mucous membranes with strong irritant effect on the eyes.
(2) It is easily flammable with the burning point being 390 ℃ and a greater risk of combustion. Its vapor can form an explosive mixture with air with the explosion limit remaining not be determined. Since the vapor is heavier than air, it can spread to a considerable distance and cause ignition of a source of fire and further propagate the flame back. It can have violent reaction when coming across water and alcohol. When being heated to decomposition, it can release HCl and highly toxic phosgene gas.
[The main purpose]

Acetyl chloride is the most commonly used acetylating agent with reaction with alcohol and phenol generating acetate ether. Its reaction with ammonia can generate acetamide with its interaction with primary amine and secondary amine to generate N-substituted acetamide.
It can be used for the manufacturing of pharmaceutical industry, pesticide manufacturing, acetyl derivatives and dyes. It can be used as the reagents for the determination of phosphorus, cholesterol, water content contained in organic solvents, nitroso, hydroxyl and tetraethyl lead.
Acetyl chloride is the most important acyl halide and can be manufactured through the reaction between glacial acetic acid and thionyl chloride or phosphorus trichloride and phosphorus pentachloride.
The above information is edited by Andy from ChemicalBook.
[Harmful effects and symptoms of poisoning]

Acetyl chloride is a kind of stimulant and corrosive with contact with the skin being able to cause burns. Its steam can strongly irritate the eye and mucous membranes. Human’s inhalation of 2 ppm will be able to feel stimulating effect. Short-term exposure to higher concentrations of acetyl chloride may cause death or permanent damage. The poisoning amount of the aquatic animal is estimated to be in the range of 10 to 100 ppm.
[Chemical properties]

It appears as colorless transparent liquid smoke with irritating smell. It is miscible with ether, acetic acid and benzene.
[Uses]

1.   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.
[Production method]

Industrial, acetyl chloride can be manufactured through the reaction between ethylene with hydrogen chloride, or the reaction between sodium acetate, sulfur dioxide and chlorine. The laboratory can apply acetic acid, sodium acetate or acetic anhydride to have reaction with a variety of chlorination agents. For example, it can be obtained through the reaction between acetic anhydride with chlorosulfonic acid (or hydrogen chloride, carbon tetrachloride, phosgene); or obtained through the reaction between glacial acetic acid and benzoyl chloride (or silicon tetrachloride, phosphorus trichloride, chlorinated sulfurous acid and phosphorus pentachloride,). OPERATION EXAMPLE 1: Ingredient ratio (molar ratio): glacial acetic acid: phosphorus trichloride = 3: 1.2. Glacial acetic acid was added to the reactor and stirred slowly. Phosphorus trichloride was added drop-wise over 10-15 min at room temperature. The reaction mixture is subjecting to heating to increase reaction temperature and subject to reaction being maintained at 40-50 °C for 0.5 h. The reaction product is static with the separation obtaining crude product of acetyl chloride and the yield of about 70%.
Operation Example 2 Into a 3 L three-necked flask, add 360 g (6 mol) of glacial acetic acid and 552 g of toluene; heat to 50 °C, and add dropwise 510 g (3 mol) of silicon tetrachloride over 30 min. Keep the temperature at 50 ° C to until hydrogen chloride gas stops being released. Then apply fractionation, steam to until the temperature of the top of the column reaches 80-85 ℃ to obtain the crude product. The fine product is further subject to re-distillation. Take the 50-65 °C fractions and obtain 400 g of acetyl chloride with the yield being 85%. Fixed consumption amount of raw materials: glacial acetic acid: 850kg/t, phosphorus trichloride: 1950kg/t.
[Hazards & Safety Information]

Category Flammable liquids
Toxic grading poisoning
Acute Toxicity Oral-Rat LD50: 910 mg/kg
Dangerous properties of explosives being corrosive to the skin, eyes and mucous membrane;
Flammable and hazardous properties it is flammable in case of fire, high temperature and oxidant; at high temperature, it can be subject to decomposition to release toxic phosgene; it can release toxic chloride when coming across water;
Storage and transportation characteristics Treasury: ventilation, low-temperature and drying; store separately from oxidants and acids;
Extinguishing agent dry powder, dry sand, dry stone powder, carbon dioxide, foam
Spectrum DetailBack Directory
[Spectrum Detail]

Acetyl chloride(75-36-5)13CNMR
Acetyl chloride(75-36-5)IR1
Acetyl chloride(75-36-5)MS
Acetyl chloride(75-36-5)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Acetyl chloride, 99+%(75-36-5)
[Alfa Aesar]

Acetyl chloride, ACS, 98.5+%(75-36-5)
[Sigma Aldrich]

75-36-5(sigmaaldrich)
[TCI AMERICA]

Acetyl Chloride,>97.0%(T)(75-36-5)
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