Bromoacetic acid

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Bromoacetic acid
Skeletal formula of bromoacetic acid
Skeletal formula of bromoacetic acid
Ball-and-stick model
Ball-and-stick model
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 Edit this at Wikidata
EC Number
  • 201-175-8
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
  • 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[1]
1.4804 (50 °C, D)
Structure
Hexagonal or orthorhombic
Hazards
GHS labelling:[2]
GHS05: Corrosive GHS06: Toxic GHS07: Exclamation mark GHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).

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.

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 → BrCH2CO2H + HBr

See also[edit]

References[edit]

  1. ^ Dippy, J. F. J., Hughes, S. R. C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. ^ "Bromoacetic acid". PubChem.
  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. ISBN 978-3527306732.
  4. ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses; Collected Volumes, vol. 3, p. 381..

External links[edit]

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