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.

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
CAS Number
3D model (JSmol)
Beilstein Reference
 506167
ChEMBL
ChemSpider
ECHA InfoCard 100.001.069
EC Number
  • 201-175-8
PubChem CID
RTECS number
  • AF5950000
UNII
InChI
  • InChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: KDPAWGWELVVRCH-UHFFFAOYSA-N
  • InChI=1/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: KDPAWGWELVVRCH-UHFFFAOYAM
SMILES
  • C(C(=O)O)Br
  • BrCC(O)=O
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
GHS labelling:[2]
Pictograms
Signal word
 Danger
Hazard statements
 H301, H311, H314, H317, H331, H400
Precautionary statements
 P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
3
1
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

The compound is prepared by bromination of acetic acid, such as by a Hell–Volhard–Zelinsky reaction[3] or using other reagents.[4]

CH3CO2H + Br2 → CH2BrCO2H + HBr

See also

References
  1. Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. "Bromoacetic acid". pubchem.ncbi.nlm.nih.gov.
  3. 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.
  4. Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses.; Collective Volume, vol. 3, p. 381
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