Bromoacetic acid
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Names | |||
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IUPAC name
2-bromoacetic acid | |||
Other names
Bromoethanoic acid, α-Bromoacetic acid, Monobromoacetic acid, Carboxymethyl bromide, UN 1938 | |||
Identifiers | |||
506167 | |||
79-08-3 ![]() | |||
ChEMBL | ChEMBL60851 ![]() | ||
ChemSpider | 10301338 | ||
EC number | 201-175-8 | ||
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Jmol-3D images | Image Image | ||
PubChem | 6227 | ||
RTECS number | AF5950000 | ||
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Properties | |||
Molecular formula |
C2H3BrO2 | ||
Molar mass | 138.95 g·mol−1 | ||
Appearance | White to light yellow crystalline solid | ||
Density | 1.934 g/mL | ||
Melting point | 49 to 51 °C (120 to 124 °F; 322 to 324 K) | ||
Boiling point | 206 to 208 °C (403 to 406 °F; 479 to 481 K) | ||
polar organic solvents | |||
Acidity (pKa) | 2.86[1] | ||
Refractive index (nD) |
1.4804 (50 °C, D) | ||
Structure | |||
Crystal structure | Hexagonal or orthorhombic | ||
Hazards | |||
Main hazards | Toxic (T), Corrosive (C) | ||
R-phrases | R23/24/25, R36 | ||
S-phrases | S36/37/39, S45 | ||
NFPA 704 | |||
Flash point | 110 °C (230 °F; 383 K) | ||
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |||
Infobox references | |||
Bromoacetic acid is the chemical compound with the formula CH2BrCO2H. This colorless solid is a relatively strong alkylating agent. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example in pharmaceutical chemistry.
The compound is prepared by bromination of acetic acid.[2]
- CH3COOH + Br2 → CH2BrCOOH + HBr
It can also be prepared by the Hell-Volhard-Zelinsky process:
- CH3COOH + Br2 + Red Phosphorus → CH2BrCOOH
See also
References
- ↑ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
- ↑ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Org. Synth.; Coll. Vol. 3, p. 381