Acetyl bromide

Structural formula
General
Surname	Acetyl bromide
other names	Acetic acid bromide; Acetoxybromide;
Molecular formula	C 2 H 3 BrO
Brief description	highly volatile, yellowish liquid with a pungent odor
External identifiers / databases
EC number	208-061-7
ECHA InfoCard	100.007.329
PubChem	10482
Wikidata	Q420493
properties
Molar mass	122.95 g mol −1
Physical state	liquid
density	1.65 g cm −3
Melting point	−96 ° C
boiling point	76.7 ° C
Vapor pressure	133 mbar (20 ° C)
solubility	decomposes in water with violent reaction
Refractive index	1.4537 (at 16 ° C, 589 nm)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 290-314
	EUH: 014
	P: 280-301 + 330 + 331-305 + 351 + 338-308 + 310
Thermodynamic properties
ΔH f 0	−223.5 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Acetyl bromide is a chemical compound from the group of carboxylic acid halides and organic bromine compounds .

Extraction and presentation

Acetyl bromide can be made by reacting phosphorus tribromide and acetic acid :

${\ displaystyle \ mathrm {3 \ CH_ {3} COOH + PBr_ {3} \ longrightarrow 3 \ CH_ {3} COBr + H_ {3} PO_ {3}}}$

properties

Acetyl bromide is a volatile, colorless to yellowish liquid that smokes in the air and has a pungent odor. When heated or in contact with water or lower alcohols , it decomposes with a violent reaction, producing hydrogen bromide .

use

Acetyl bromide is mainly used as an acetylating agent in organic synthesis.

safety instructions

The vapors of acetyl bromide can form an explosive mixture with air ( flash point 75 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on acetyl bromide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Acetyl bromide data sheet (PDF) from Merck , accessed October 30, 2011.

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-21.

^ Theodore M. Burton and Ed. F. Degering: The Preparation of Acetyl Bromide . In: J. Am. Chem. Soc. . 62, 1940, p. 227. doi : 10.1021 / ja01858a502 .

↑ ^a ^b Wissenschaft-online.de: Entry on acetyl bromide in the Lexikon Chemie, accessed on January 21, 2018

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on acetyl bromide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Merck-2] Acetyl bromide data sheet (PDF) from Merck , accessed October 30, 2011.

[CRC90_5_21-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-21.

[4] Theodore M. Burton and Ed. F. Degering: The Preparation of Acetyl Bromide . In: J. Am. Chem. Soc. . 62, 1940, p. 227. doi : 10.1021 / ja01858a502 .

[lc-5] Wissenschaft-online.de: Entry on acetyl bromide in the Lexikon Chemie, accessed on January 21, 2018