3-bromobutyric acid

Structural formula
General
Surname	3-bromobutyric acid
other names	3-bromobutanoic acid ( IUPAC )
Molecular formula	C 4 H 7 BrO 2
Brief description	clear, colorless to yellow liquid with an unpleasant odor
External identifiers / databases
CAS number 2623-86-1 EC number 220-082-3 ECHA InfoCard 100.018.258 PubChem 102860 ChemSpider 92918 Wikidata Q223055
properties
Molar mass	167.00 g · mol -1
Physical state	liquid
density	1.57 g cm −3 (20 ° C)
Melting point	17 ° C
boiling point	114–115 ° C (2 mmHg)
Refractive index	1.476 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314 P: 280-305 + 351 + 338-310
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

3-bromobutyric acid is a halogenated aliphatic carboxylic acid that is derived from butyric acid.

Manufacturing

3-Bromobutyric acid can be obtained by the electrophilic addition of hydrogen bromide to crotonic acid . The direction of substitution results from the electron-withdrawing effect of the carboxy group , which means that the more stable carbenium ion is formed at position 3 , to which the bromine attaches.

properties

3-Bromobutyric acid contains a stereocenter , so it is chiral . Racemic 3-bromobutyric acid [synonym: ( RS ) -3-bromobutyric acid] is a 1: 1 mixture of ( R ) -3-bromobutyric acid and ( S ) -3-bromobutyric acid. Their flash point is 114 ° C.

Individual evidence

1. ↑ Data sheet 3-bromobutyric acid from Acros, accessed on May 20, 2010.
2. ↑ Data sheet 3-bromobutyric acid from AlfaAesar, accessed on May 20, 2010 ( PDF )(JavaScript required) .
3. ^ ^{A b} Arthur Michael, Howard S. Mason: Normal Addition of Hydrogen Bromide to 3-Butenoic, 4-Pentenoic and 5-Hexenoic Acids in Hexane. In: Journal of the American Chemical Society No. 65, 1943, p. 683.
4. ↑ ^{a b c d} data sheet 3-Bromobutyric acid from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).