Misplaced Pages

2-Bromobutyric acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from 2-bromobutyric acid) Chemical compound
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.177 Edit this at Wikidata
EC Number
  • 201-294-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • CCC(Br)C(=O)O
Properties
Chemical formula C4H7BrO2
Molar mass 167.002 g·mol
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
Solubility in water 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:
Pictograms GHS05: Corrosive GHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H314
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

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

Production

(±)-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.

References

  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.
Categories: