Bromoacetic acid

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Bromoacetic acid
Skeletal formula of bromoacetic acid Ball-and-stick model
Identifiers
CAS number 79-08-3 YesY
PubChem 6227
ChemSpider 10301338
EC number 201-175-8
ChEMBL CHEMBL60851 YesY
RTECS number AF5950000
Beilstein Reference 506167
Jmol-3D images Image 1
Properties
Molecular formula 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)
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
R-phrases R23/24/25, R36
S-phrases S36/37/39, S45
Main hazards Toxic (T), Corrosive (C)
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 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.[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: 381 

External links[edit]