ω-bromoacetophenone

Structural formula
General
Surname	ω-bromoacetophenone
other names	Phenacyl bromide; 2-bromo-1-phenylethanone; α-bromoacetophenone;
Molecular formula	C 8 H 7 BrO
Brief description	colorless solid
External identifiers / databases
EC number	200-724-9
ECHA InfoCard	100,000,659
PubChem	6259
Wikidata	Q310709
properties
Molar mass	199.05 g mol −1
Physical state	firmly
density	1.65 g cm −3
Melting point	48-51 ° C
boiling point	140 ° C (15 h Pa )
Vapor pressure	16 h Pa (134 ° C)
solubility	almost insoluble in water; soluble in ethanol , chloroform and diethyl ether ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 302 + 352-304 + 340-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

ω-Bromoacetophenone is a strong eye-irritating chemical compound, which is only slightly inferior to chloroacetophenone in its eye-irritating effect .

presentation

ω-bromoacetophenone was first characterized in 1871 by A. Emmerling and C. Engler as “bromine acetophenone”.

The preparation is easily possible by acid-catalyzed bromination of acetophenone or by Friedel-Crafts acylation of benzene with bromoacetyl bromide in the presence of aluminum chloride as a catalyst.

properties

From a chemical point of view, ω-bromoacetophenone is an aliphatic-aromatic ketone . As a pure substance, ω-bromoacetophenone is in the form of colorless rhombic crystals; the light-sensitive product is often yellow-brown in color. In the presence of bases such as sodium ethoxide, "phenacyl bromide" is converted into "bromodiphenacyl" by aldol condensation.

ω-bromoacetophenone is very irritating to the skin and eyes.

use

ω-Bromoacetophenone is mainly used as an intermediate in the production of pharmaceuticals and other chemical compounds (for example indoles by the Bischler-Möhlau indole synthesis ).

It can be used for the derivatization of carboxylic acids (by ester formation at pH 8.5).

literature

Beilstein, Syst. No. 639, Volume 7, H 283f , EI 152

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-bromoacetophenone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b Entry on ω- (or α-) bromoacetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on May 14, 2014.
↑ A. Emmerling, C. Engler: About some derivatives of acetophenone . In: Reports of the German Chemical Society in Berlin 4 , 147–149 (1871).
^ RL Cowper, LH Davidson: Phencyl Bromide [Acetopheone, α-bromo-] Template: Linktext-Check / Escaped In: Organic Syntheses . 19, 1939, p. 24, doi : 10.15227 / orgsyn.019.0024 ; Coll. Vol. 2, 1943, p. 480 ( PDF ).
↑ Oskar Widman: About the constitution of the so-called α- and β-halodiphenacyls . In: Justus Liebigs Annalen der Chemie 400 , 86-130 (1913), doi : 10.1002 / jlac.19134000107 .
↑ J. Bodoprost, H. Rosemeyer: Analysis of Phenacyl Ester Derivatives of Fatty Acids . In: Int. J. Mol. Sci. 2007, 8, 1111-1124.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-bromoacetophenone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[roempp-2] Entry on ω- (or α-) bromoacetophenone. In: Römpp Online . Georg Thieme Verlag, accessed on May 14, 2014.

[3] A. Emmerling, C. Engler: About some derivatives of acetophenone . In: Reports of the German Chemical Society in Berlin 4 , 147–149 (1871).

[4] RL Cowper, LH Davidson: Phencyl Bromide [Acetopheone, α-bromo-] Template: Linktext-Check / Escaped In: Organic Syntheses . 19, 1939, p. 24, doi : 10.15227 / orgsyn.019.0024 ; Coll. Vol. 2, 1943, p. 480 ( PDF ).

[5] Oskar Widman: About the constitution of the so-called α- and β-halodiphenacyls . In: Justus Liebigs Annalen der Chemie 400 , 86-130 (1913), doi : 10.1002 / jlac.19134000107 .

[6] J. Bodoprost, H. Rosemeyer: Analysis of Phenacyl Ester Derivatives of Fatty Acids . In: Int. J. Mol. Sci. 2007, 8, 1111-1124.