2-Bromobutyric acid is the organic compound with the molecular formula CH3CH2CH(Br)CO2H. It is a colorless liquid.

2-Bromobutyric acid
Names
Preferred IUPAC name
2-Bromobutanoic acid
Other names
2-Bromobutyric acid
alpha-Bromobytyric acid
dl-2-Bromobutyric acid
α-Bromobutyricacid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.177 Edit this at Wikidata
EC Number
  • 201-294-5
UNII
  • InChI=1S/C4H7BrO2/c1-2-3(5)4(6)7/h3H,2H2,1H3,(H,6,7)
    Key: YAQLSKVCTLCIIE-UHFFFAOYSA-N
  • InChI=1/C4H7BrO2/c1-2-3(5)4(6)7/h3H,2H2,1H3,(H,6,7)
    Key: YAQLSKVCTLCIIE-UHFFFAOYAL
  • CCC(Br)C(=O)O
Properties
C4H7BrO2
Molar mass 167.002 g·mol−1
Appearance colorless liquid
Density 1.567 g/mL at 25 °C
Melting point −4 °C (25 °F; 269 K) racemate
Boiling point 99 to 103 °C (210 to 217 °F; 372 to 376 K) 10 mmHg
66 g/L (20 °C)
Vapor pressure 0.0533 Torr
Acidity (pKa) 2.95±0.10. Most Acidic Temp: 25 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed.
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Danger
H302, H314
P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
Flash point > 112 °C (234 °F; 385 K)
Related compounds
Other anions
2-Bromobutyride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The 2-position is stereogenic, so the compound is chiral. Optical resolution can be effected using strychnine.[1]

2-Bromobutyric acid is used as a building block chemical, such as in the preparation of Levetiracetam,[citation needed] an anticonvulsant medication.[2]

Production

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(±)-2-Bromobuyric acid may be prepared by the acid-catalyzed Hell–Volhard–Zelinsky reaction, where butyric acid is treated with elemental bromine. It is one of many compounds that arise adventiously from the use of bromine as an antiseptic.[3]

 

References

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  1. ^ Ahlberg, R. (1932). "Über die α-Brom-n-buttersäure. (II. Mitteilung). Die Zerlegung der racem-Säure". Journal für Praktische Chemie. 135 (11–12): 335–344. doi:10.1002/prac.19321351103.
  2. ^ "Levetiracetam - PubMed Health". Archived from the original on 2012-11-30. Retrieved 2017-11-01.
  3. ^ Krasner, Stuart W.; Weinberg, Howard S.; Richardson, Susan D.; Pastor, Salvador J.; Chinn, Russell; Sclimenti, Michael J.; Onstad, Gretchen D.; Thruston, Alfred D. (2006). "Occurrence of a New Generation of Disinfection Byproducts". Environmental Science & Technology. 40 (23): 7175–7185. doi:10.1021/es060353j. PMID 17180964.