2-Bromobutyric acid

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	80-58-0 racemic ; 2681-94-9 R enantiomer; 32659-49-7 S enantiomer;
3D model (JSmol)	Interactive image;
ChemSpider	6403;
ECHA InfoCard	100.001.177
EC Number	201-294-5;
PubChem CID	6655;
UNII	MCO6PW23BT ;
CompTox Dashboard (EPA)	DTXSID90861642 ;
	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−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
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
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 [77 °F], 100 kPa). Infobox references

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, an anticonvulsant medication.^[2]

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.^[3]

References

↑ 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.

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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.

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