Acetyl bromide

Acetyl bromide[1]
Structural formula of acetyl bromide	Ball-and-stick model of acetyl bromide
Names
	Preferred IUPAC name Acetyl bromide
Identifiers
CAS Number	506-96-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	10050 ;
ECHA InfoCard	100.007.329
EC Number	208-061-7;
PubChem CID	10482;
RTECS number	AO5955000;
UNII	O18V5XYO0G;
UN number	1716
CompTox Dashboard (EPA)	DTXSID5060140 ;
	InChI InChI=1S/C2H3BrO/c1-2(3)4/h1H3 Key: FXXACINHVKSMDR-UHFFFAOYSA-N ; InChI=1/C2H3BrO/c1-2(3)4/h1H3 Key: FXXACINHVKSMDR-UHFFFAOYAZ;
	SMILES CC(=O)Br; BrC(=O)C;
Properties
Chemical formula	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
Safety data sheet	ILO MSDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501
Flash point	110 °C (230 °F; 383 K)
	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 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

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

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

[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.