Bromoacetic acid

Bromoacetic acid is the chemical compound with the formula BrCH2CO2H. 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
Names
Preferred IUPAC name
Bromoacetic acid
Other names
  • 2-Bromoacetic acid
  • Bromoethanoic acid
  • α-Bromoacetic acid
  • Carboxymethyl bromide
  • Monobromoacetic acid
  • UN 1938
Identifiers
3D model (JSmol)
506167
ChEMBL
ChemSpider
ECHA InfoCard 100.001.069
EC Number
  • 201-175-8
PubChem CID
RTECS number
  • AF5950000
UNII
  • 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
BrCH2CO2H
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 Polar organic solvents
Acidity (pKa) 2.86
Refractive index (nD)
1.4804 (50 °C, D)
Structure
Hexagonal or orthorhombic
Hazards
GHS labelling:
Danger
H301, H311, H314, H317, H331, H400
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)
Related compounds
Related compounds
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 or using other reagents.

CH3CO2H + Br2 → BrCH2CO2H + HBr
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