Bromoacetic acid

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Bromoacetic acid
Skeletal formula of bromoacetic acid 2-bromoacetic acid 200.svg
Skeletal formula of bromoacetic acid
Ball-and-stick model Bromoacetic-acid-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-175-8
PubChem CID
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
AppearanceWhite 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]
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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.svgHealth 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)
Related compounds
Related compounds
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 Br C H 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]

CH3CO2H + Br2 → BrCH2CO2H + HBr

Related Research Articles

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<span class="mw-page-title-main">Acetoacetic acid</span> Chemical compound

Acetoacetic acid is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid.

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(<i>E</i>)-Stilbene Chemical compound

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References

  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..