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Line 25: Line 25:
| C = 2 | H = 3 | Br = 1 | O = 2
| C = 2 | H = 3 | Br = 1 | O = 2
| Appearance = White to light yellow crystalline solid
| Appearance = White to light yellow crystalline solid
| Density = 1.934 g&bull;cm<sup>-3</sup>
| Density = 1.934 g/mL
| MeltingPt = 49 - 51 °C
| MeltingPt = 49 - 51 °C
| BoilingPt = 206 - 208 °C
| BoilingPt = 206 - 208 °C

Revision as of 18:55, 24 October 2011

Bromoacetic acid
Skeletal formula of bromoacetic acid
Skeletal formula of bromoacetic acid
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
2-bromoacetic acid
Other names
Bromoethanoic acid, α-Bromoacetic acid, Monobromoacetic acid, Carboxymethyl bromide, UN 1938
Identifiers
3D model (JSmol)
506167
ChEMBL
ECHA InfoCard 100.001.069 Edit this at Wikidata
EC Number
  • 201-175-8
RTECS number
  • AF5950000
  • InChI=1/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
  • C(C(=O)O)Br
Properties
C2H3BrO2
Molar mass 138.948 g·mol−1
Appearance White to light yellow crystalline solid
Density 1.934 g/mL
Melting point 49 - 51 °C
Boiling point 206 - 208 °C
polar organic solvents
Acidity (pKa) 2.86[1]
1.4804 (50 °C, D)
Structure
Hexagonal or orthorhombic
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic (T), Corrosive {C)
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
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 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.[2]

CH3CO2H + Br2 → CH2BrCO2H + HBr

See also

References

  1. ^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3, p. 381.
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