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Acetyl chloride information


Acetyl chloride[1]
Skeletal formula of acetyl chloride
Skeletal formula of acetyl chloride
Ball-and-stick model of acetyl chloride
Ball-and-stick model of acetyl chloride
Space-filling model of acetyl chloride
Names
Preferred IUPAC name
Acetyl chloride[2]
Systematic IUPAC name
Ethanoyl chloride
Other names
Acyl chloride
Identifiers
CAS Number
  • 75-36-5 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
605303
ChEBI
  • CHEBI:37580 checkY
ChemSpider
  • 6127 checkY
ECHA InfoCard 100.000.787 Edit this at Wikidata
EC Number
  • 200-865-6
Gmelin Reference
1611
PubChem CID
  • 6367
RTECS number
  • AO6390000
UNII
  • QD15RNO45K checkY
UN number 1717
CompTox Dashboard (EPA)
  • DTXSID2023852 Edit this at Wikidata
InChI
  • InChI=1S/C2H3ClO/c1-2(3)4/h1H3 checkY
    Key: WETWJCDKMRHUPV-UHFFFAOYSA-N checkY
  • InChI=1/C2H3ClO/c1-2(3)4/h1H3
    Key: WETWJCDKMRHUPV-UHFFFAOYAQ
SMILES
  • ClC(=O)C
Properties
Chemical formula
CH3COCl
Molar mass 78.49 g/mol
Appearance Colorless liquid
Density 1.104 g/ml, liquid
Melting point −112 °C (−170 °F; 161 K)
Boiling point 52 °C (126 °F; 325 K)
Solubility in water
Reacts with water
Magnetic susceptibility (χ)
-38.9·10−6 cm3/mol
Structure
Dipole moment
2.45 D
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H225, H302, H314, H335, H412
Precautionary statements
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
3
2
W
Flash point 4 °C (39 °F; 277 K)
Autoignition
temperature
390 °C (734 °F; 663 K)
Explosive limits 7.3–19%
Related compounds
Related acyl chlorides
Propionyl chloride
Butyryl chloride
Related compounds
Acetic acid
Acetic anhydride
Acetyl bromide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid (CH3COOH). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

  1. ^ Merck Index, 11th Edition, 79.
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 796–797. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

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Acetyl chloride

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Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid (CH3COOH). It belongs to the class of organic compounds called acid halides. It...

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Acyl chloride

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example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides. Where the acyl chloride moiety takes...

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Acetyl group

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variety of methods, most commonly with the use of acetic anhydride or acetyl chloride, often in the presence of a tertiary or aromatic amine base. A typical...

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Acetic acid

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industrial uses, but it is by far the oldest and best-known application. acetyl chloride SOCl2 acetic acid (i) Li[AlH4], ether (ii) H3O+ ethanol Acetic acid...

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Phenyl acetate

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acid. It can be produced by reacting phenol with acetic anhydride or acetyl chloride. Phenyl acetate can be separated into phenol and an acetate salt, via...

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Acetic anhydride

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methyl iodide in turn affords acetyl iodide, which reacts with acetate salts or acetic acid to give the product. Rhodium chloride in the presence of lithium...

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Peracetic acid

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strong acid catalyst will not form peracetic acid. As an alternative, acetyl chloride and acetic anhydride can be used to generate a solution of the acid...

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Triphenylmethyl chloride

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group. Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts...

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Trifluoroacetyl chloride

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Trifluoroacetyl chloride (also known as TFAC) is a toxic gaseous chemical compound with the chemical formula C2ClF3O. TFAC is the perfluorinated version of acetyl chloride...

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Acetate

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(biochemistry) Sodium acetate Mixed acid fermentation Acetic acid Acetyl chloride Zinc acetate Zumdahl, S. S. “Chemistry” Heath, 1986: Lexington, MA...

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Cadmium chloride

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also be prepared from anhydrous cadmium acetate using hydrogen chloride or acetyl chloride. Industrially, it is produced by the reaction of molten cadmium...

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Trichloroacetyl chloride

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Trichloroacetyl chloride is the acyl chloride of trichloroacetic acid. It can be formed by reacting chlorine with acetyl chloride or acetaldehyde in the...

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Aspirin

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Charles Frédéric Gerhardt treated the medicine sodium salicylate with acetyl chloride to produce acetylsalicylic acid for the first time. Over the next 50...

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Acetyl iodide

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Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger...

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Aniline

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a protection with acetyl chloride is required: The reaction to form 4-bromoaniline is to protect the amine with acetyl chloride, then hydrolyse back...

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Pyruvic acid

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permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:[citation needed] CH3COCl...

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Acetylation

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cogenerates acetic acid. Acetyl chloride. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable...

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Acyl group

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bond. Well-known acyl compounds are the acyl chlorides, such as acetyl chloride (CH3COCl) and benzoyl chloride (C6H5COCl). These compounds, which are treated...

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Acyl halide

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hydrogen chloride produces a mixture of acetyl chloride and acetic acid: (CH3CO)2O + HCl → CH3COCl + CH3CO2H Common syntheses of acyl chlorides also entail...

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Acetyl nitrate

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nitrolysis reactions. It acetylates amines, akin to the behavior of acetyl chloride: 2 NH 3 + CH 3 C ( O ) ONO 2 ⟶ NH 4 NO 3 + CH 3 CONH 2 {\displaystyle...

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Acylation

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Friedel–Crafts acylation uses acetyl chloride (CH3COCl) as the agent and aluminum chloride (AlCl3) as a catalyst to add an acetyl group to benzene: This reaction...

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Acetylcholine

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by the enzyme choline acetyltransferase from the compounds choline and acetyl-CoA. Cholinergic neurons are capable of producing ACh. An example of a central...

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Anilide

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Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chloride provides acetanilide (CH3−CO−NH−C6H5)...

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Acetoxy group

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alcohol (in effect protecting the alcohol by acetylation): Acetyl halide, such as acetyl chloride in the presence of a base like triethylamine Activated ester...

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Chloroacetic acid

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et sur le chlorure d'acétyle" (in French) (Note on aldehyde and on acetyl chloride), Annales de chimie et de physique, 3rd series, 49 : 58–62, see p. 61...

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Acetanisole

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prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride: It is used as a cigarette additive, a fragrance, and a flavoring in...

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