Bromoacetic acid

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Bromoacetic acid
Skeletal formula of bromoacetic acid
Ball-and-stick model
Names
Preferred IUPAC name
Bromoacetic acid
Other names
2-Bromoacetic acid
Bromoethanoic acid
α-Bromoacetic acid
Monobromoacetic acid
Carboxymethyl bromide
UN 1938
Identifiers
3D model (JSmol)
506167
ChEMBL
ChemSpider
ECHA InfoCard 100.001.069
EC Number
  • 201-175-8
RTECS number
  • AF5950000
Properties
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)
polar organic solvents
Acidity (pKa) 2.86[1]
1.4804 (50 °C, D)
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R-phrases (outdated) R23/24/25, R36
S-phrases (outdated) S36/37/39, S45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)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
3
0
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

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, such as by a Hell–Volhard–Zelinsky reaction[2] or using other reagents.[3]

CH3CO2H + Br2 → CH2BrCO2H + HBr

See also[edit]

References[edit]

  1. ^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. ^ 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.
  3. ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses.; Collective Volume, 3, p. 381

External links[edit]