Bromoacetic acid

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
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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

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[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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