Bromoacetic acid

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Bromoacetic acid
Skeletal formula of bromoacetic acid
Ball-and-stick model
Names
IUPAC name
2-bromoacetic acid
Other names
Bromoethanoic acid, α-Bromoacetic acid, Monobromoacetic acid, Carboxymethyl bromide, UN 1938
Identifiers
506167
79-08-3 N
ChEMBL ChEMBL60851 YesY
ChemSpider 10301338
EC number 201-175-8
Jmol-3D images Image
Image
PubChem 6227
RTECS number AF5950000
Properties
C2H3BrO2
Molar mass 138.95 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)
polar organic solvents
Acidity (pKa) 2.86[1]
1.4804 (50 °C, D)
Structure
Crystal structure Hexagonal or orthorhombic
Hazards
Main hazards Toxic (T), Corrosive (C)
R-phrases R23/24/25, R36
S-phrases S36/37/39, S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 110 °C (230 °F; 383 K)
Except where noted otherwise, data is 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.[2]

CH3COOH + Br2 → CH2BrCOOH + HBr

It can also be prepared by the Hell-Volhard-Zelinsky process:

CH3COOH + Br2 + Red Phosphorus → CH2BrCOOH

See also[edit]

References[edit]

  1. ^ Dippy, J.F.J., Hughes, S.R.C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Org. Synth. ; Coll. Vol. 3, p. 381 

External links[edit]