Bromoacetic acid
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.
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Names | |||
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Preferred IUPAC name
Bromoacetic acid | |||
Other names
2-Bromoacetic acid Bromoethanoic acid α-Bromoacetic acid Monobromoacetic acid Carboxymethyl bromide UN 1938 | |||
Identifiers | |||
CAS Number |
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3D model (JSmol) |
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Beilstein Reference |
506167 | ||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.001.069 | ||
EC Number |
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PubChem CID |
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RTECS number |
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CompTox Dashboard (EPA) |
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InChI
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SMILES
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Properties | |||
Chemical formula |
C2H3BrO2 | ||
Molar mass | 138.948 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) | ||
Solubility in water |
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R-phrases (outdated) | R23/24/25, R36 | ||
S-phrases (outdated) | S36/37/39, S45 | ||
NFPA 704 (fire diamond) | |||
Flash point | 110 °C (230 °F; 383 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Infobox references | |||
The compound is prepared by bromination of acetic acid, such as by a Hell–Volhard–Zelinsky reaction[2] or using other reagents.[3]
- CH3CO2H + Br2 → CH2BrCO2H + HBr
See also
- Acetic acid
- Chloroacetic acid
- Ethyl bromoacetate
References
- Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
- Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.
- Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses.; Collective Volume, 3, p. 381
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