Acetyl bromide

Acetyl bromide is an acyl bromide compound. As is expected, it may be prepared by reaction between phosphorus tribromide and acetic acid:[2]

3 CH3COOH + PBr3 → 3 CH3COBr + H3PO3
Acetyl bromide[1]
Structural formula of acetyl bromide
Ball-and-stick model of acetyl bromide
Names
Preferred IUPAC name
Acetyl bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.329
EC Number
  • 208-061-7
RTECS number
  • AO5955000
UNII
UN number 1716
  • InChI=1S/C2H3BrO/c1-2(3)4/h1H3 checkY
    Key: FXXACINHVKSMDR-UHFFFAOYSA-N checkY
  • InChI=1/C2H3BrO/c1-2(3)4/h1H3
    Key: FXXACINHVKSMDR-UHFFFAOYAZ
  • CC(=O)Br
  • BrC(=O)C
Properties
C2H3BrO
Molar mass 122.949 g·mol−1
Density 1.663 g/mL
Melting point −96 °C (−141 °F; 177 K)
Boiling point 75 to 77 °C (167 to 171 °F; 348 to 350 K)
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Flash point 110 °C (230 °F; 383 K)
Safety data sheet (SDS) ILO MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

As usual for an acid halide, acetyl bromide hydrolyzes rapidly in water, forming acetic acid and hydrobromic acid. It also reacts with alcohols and amines to produce acetate esters and acetamides, respectively.

References
  1. Acetyl bromide at Sigma-Aldrich
  2. Theodore M. Burton and Ed. F. Degering (1940). "The Preparation of Acetyl Bromide". J. Am. Chem. Soc. 62: 227. doi:10.1021/ja01858a502.
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