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320129

Sigma-Aldrich

Acetyl chloride

reagent grade, 98%

Synonym(s):

Acetic acid chloride, Acetic chloride, Ethanoyl chloride

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About This Item

Linear Formula:
CH3COCl
CAS Number:
Molecular Weight:
78.50
Beilstein:
605303
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

reagent grade

Quality Level

vapor density

2.7 (vs air)

vapor pressure

11.69 psi ( 20 °C)
32.33 psi ( 55 °C)

Assay

98%

form

liquid

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.

Application

  • Synthesis, Characterization, and Evaluation of Thiazolidine Derivatives of Cysteine for Suppressing Eumelanin Production.: The study discusses the synthesis and evaluation of thiazolidine derivatives of cysteine, where acetyl chloride is used as a reagent, underscoring its importance in pharmaceutical intermediate development. (Amino et al., 2016).
  • New URJC-1 Material with Remarkable Stability and Acid-Base Catalytic Properties.: This research introduces the new URJC-1 material, noting its stability and catalytic properties, with acetyl chloride being pivotal in the synthesis process, illustrating its role in material science and catalysis. (Leo et al., 2016).

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

41.0 °F - closed cup

Flash Point(C)

5 °C - closed cup


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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)
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
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)
Oxetanes. VII. Synthesis from 1, 3-Diols. Reactions of Oxetanes and of 1, 3-Butanediol with Hydrogen Chloride, Hydrogen Bromide and Acetyl Chloride1, 2.
Searles JS, et al.
Journal of the American Chemical Society, 79(4), 952-956 (1957)

Articles

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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