Acetyl chloride

Acetyl chloride

Names
Preferred IUPAC name Acetyl chloride
Systematic IUPAC name Ethanoyl chloride
Other names Acyl chloride
Identifiers
CAS Number	75-36-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:37580 Y
ChemSpider	6127 Y
ECHA InfoCard	100.000.787
RTECS number	AO6390000
UNII	QD15RNO45K Y
InChI InChI=1S/C2H3ClO/c1-2(3)4/h1H3 Y Key: WETWJCDKMRHUPV-UHFFFAOYSA-N Y 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
EU classification (DSD)	Flammable (F) Corrosive (C)
R-phrases	R11 R14 R34
S-phrases	(S1/2) S9 S16 S26 S45
NFPA 704	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).
Y  (what is YN ?)
Infobox references

Acetyl chloride, CH₃COCl is an acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless, corrosive, volatile liquid.

Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by reacting potassium acetate with phosphoryl chloride.

Acetyl chloride mixed with acetic acid is produced by the reaction of acetic anhydride with hydrogen chloride:

Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as PCl₃, PCl₅, SO₂Cl₂, or SOCl₂. However, these methods usually gives acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. a route avoiding these impurities of phosphorus and sulphur is that of phosgene and acetic acid, COCl₂ + CH₃COOH = CH₃COCl + HCl + CO₂. HCl impurities can be removed by distilling the crude product from dimethylaniline or by degassing the mixture by a stream of argon.

When heated, a mixture of dichloroacetic acid and acetic acid gives acetyl chloride. It can also be synthesized from the catalytic carbonylation of methyl chloride.