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320129

Sigma-Aldrich

Acetyl chloride

reagent grade, 98%

Linear Formula:
CH3COCl
CAS Number:
Molecular Weight:
78.50
Beilstein:
605303
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

vapor density

2.7 (vs air)

vapor pressure

11.69 psi ( 20 °C)
32.33 psi ( 55 °C)

assay

98%

autoignition temp.

1353 °F

expl. lim.

19 %

refractive index

n20/D 1.389 (lit.)

bp

52 °C (lit.)

mp

−112 °C (lit.)

density

1.104 g/mL at 25 °C (lit.)

SMILES string

CC(Cl)=O

InChI

1S/C2H3ClO/c1-2(3)4/h1H3

InChI key

WETWJCDKMRHUPV-UHFFFAOYSA-N

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General description

Acetyl chloride undergoes reaction with decalin and aluminum trichloride to afford a tricyclic enol ether. It promotes the cyclopropanation of alkene with dibromomethane or diiodomethane in the presence of Zn dust and copper chloride in ether. Friedel-Crafts reaction of acetyl chloride with benzene in the presence of MCl3 (M = Al or Fe) in the ionic liquid 1-butyl-3-methylimidazolium chloride affords MCl3 adducts of the acetyl chloride, the acetylium ion [CH3CO]+[MCl4]- and the MCl3 adduct of acetophenone.

Packaging

1 kg in PVC-coated bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK Germany

WGK 1

Flash Point(F)

41.0 °F - closed cup

Flash Point(C)

5 °C - closed cup

Certificate of Analysis

Certificate of Origin

In situ infrared spectroscopic studies of the Friedel-Crafts acetylation of benzene in ionic liquids using AlCl3 and FeCl3.
Csihony S, et al.
Green Chemistry, 3(6), 307-309 (2001)
Acetyl chloride promoted cyclopropanations of alkenes with dibromomethane using zinc dust and copper (I) chloride in ether.
Friedrich EC and Lewis EJ.
The Journal of Organic Chemistry, 55(8), 2491-2494 (1990)
Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl 2? 8H 2 O and acetyl chloride in solution and in solvent-free conditions.
Ghosh R, et al.
Tetrahedron Letters, 46(1), 147-151 (2005)
Catherine L Lyall et al.
Journal of the American Chemical Society, 136(39), 13745-13753 (2014-09-10)
Decalin undergoes reaction with aluminum trichloride and acetyl chloride to form a tricyclic enol ether in good yield, as first reported by Baddeley. This eye-catching transformation, which may be considered to be an aliphatic Friedel-Crafts reaction, has not previously been...
Ran Lin et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(45), 14885-14899 (2014-09-16)
Treatment of Na[Re(CO)5 ] with RCCCO2 Et (R=phenyl, naphthalen-1-yl, phenanthren-9-yl and pyren-1-yl) followed by reaction with acetyl chloride and ethanol afforded the rhenacyclobutadienes Re{-C(R)C(CO2 Et)C(OEt)}(CO)4 . Reactions of these rhenacyclobutadienes with HCCOEt produced rhenabenzenes Re{-C(R)C(CO2 Et)C(OEt)CHC(OEt)}(CO)4 . Except for R=Ph...

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

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