Acetyl chloride

Acetyl chloride[1]
Skeletal formula of acetyl chloride
Ball-and-stick model of acetyl chloride
Space-filling model of acetyl chloride
Acetyl chloride 25ml.jpg
Names
Preferred IUPAC name
Acetyl chloride[2]
Systematic IUPAC name
Ethanoyl chloride
Other names
Acyl chloride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.000.787
EC Number200-865-6
RTECS numberAO6390000
UNII
UN number1717
Properties
CH3COCl
Molar mass78.49 g/mol
AppearanceColorless liquid
Density1.104 g/ml, liquid
Melting point −112 °C (−170 °F; 161 K)
Boiling point 52 °C (126 °F; 325 K)
Reacts with water
-38.9·10−6 cm3/mol
Structure
2.45 D
Hazards
GHS pictogramsThe flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordDanger
H225, H302, H314, H318, H335, H402, H412
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+312, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P330, P363, P370+378, P403+233
NFPA 704
Flash point 4 °C (39 °F; 277 K)
390 °C (734 °F; 663 K)
Explosive limits7.3–19%
Related compounds
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 acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless, corrosive, volatile liquid.

Synthesis

Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride.[3]

The reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid:[4]

(CH3CO)2O + HCl → CH3COCl + CH3CO2H

Laboratory route

Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as PCl3, PCl5, SO2Cl2, phosgene, or SOCl2. However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions.[5]

Other methods

When heated, a mixture of dichloroacetyl chloride and acetic acid gives acetyl chloride.[5] It can also be synthesized from the catalytic carbonylation of methyl chloride.[6] It also arises from the reaction of acetic acid, acetonitrile, and hydrogen chloride.[citation needed]

Other Languages
čeština: Acetylchlorid
Deutsch: Acetylchlorid
Bahasa Indonesia: Asetil klorida
македонски: Ацетил хлорид
Nederlands: Acetylchloride
português: Cloreto de acetila
русский: Ацетилхлорид
slovenčina: Acetylchlorid
slovenščina: Acetilklorid
српски / srpski: Acetil hlorid
srpskohrvatski / српскохрватски: Acetil hlorid
svenska: Acetylklorid
українська: Ацетилхлорид
Tiếng Việt: Acetyl clorua
中文: 乙酰氯