2-Bromobutyric acid
Appearance
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Names | |||
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Preferred IUPAC name
2-Bromobutanoic acid | |||
Other names
2-Bromobutyric acid
alpha-Bromobytyric acid dl-2-Bromobutyric acid α-Bromobutyricacid | |||
Identifiers | |||
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3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.001.177 | ||
EC Number |
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PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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
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Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed. | ||
GHS labelling: | |||
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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
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2-Bromobutyride | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Bromobutyric acid is the organic compound with the molecular formula CH3CH2CH(Br)CO2H. It is a colorless liquid.
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
[edit](±)-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
[edit]- ^ 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.
- ^ "Levetiracetam - PubMed Health". Archived from the original on 2012-11-30. Retrieved 2017-11-01.
- ^ 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.