Chemistry: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
EC Number
  • 201-175-8
RTECS number
  • AF5950000
UNII
Properties
BrCH
2CO
2H
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 pictograms GHS05: Corrosive GHS06: Toxic GHS07: Harmful GHS09: Environmental hazard
GHS Signal word Danger
H301, H311, H314, H317, H331, H400
P260, P261, P264, P270, P271, P272, P273, P280, P301+310, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P311, P312, P321, P322, P330, P333+313, P361, P363, P391, P403+233
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
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

Bromoacetic acid is a chemical compound with the formula BrCH
2CO
2H. 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]

CH
3CO
2H + Br
2 → BrCH
2CO
2H + HBr

References

  1. ↑ Dippy, J. F. J., Hughes, S. R. C., Rozanski, A., J. Chem Soc., 1959, 2492.
  2. ↑ "Bromoacetic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/6227#section=GHS-Classification. 
  3. ↑ Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C.. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. 
  4. ↑ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv3p0381. ; Collective Volume, 3, pp. 381 .



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