Ethyl bromoacetate



Ethyl bromoacetate
IUPAC name Ethyl bromoacetate
Other names Bromoacetic acid
ethyl ester, Antol,
(Ethoxycarbonyl)-
methyl bromide
Identifiers
CAS number 105-36-2
RTECS number AF6000000
SMILES BrC(CO)OCC
Properties
Molecular formula C4H7O2Br
Molar mass 167.01 g/mol
Appearance colourless to yellow liquid
Density 1.51 g/cm3, liquid
Melting point

-38 °C (199 K)

Boiling point

158 °C (431 K)

Solubility in water Insoluble
Hazards
EU classification Very toxic (T+)
NFPA 704
0
3
0
 
R-phrases R26/27/28
S-phrases S45
Flash point 47 °C
Related Compounds
Other anions Ethyl acetoacetate
Ethyl iodoacetate
Related esters Methyl bromoacetate
Related compounds Chloropicrin
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Ethyl 2-bromoacetate is the acetic acid[1]

Applications

In World War I, ethyl bromoacetate was used as a chemical weapons in 1915.[2]

In carbonyl compounds to give a β-hydroxy-esters.

It is also the starting point for the preparation of several other reagents. For example, the related benzaldehyde:[1]


References

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.
  1. ^ Natelson, S.; Gottfried, S. "Ethyl Bromoacetate" Organic Syntheses, Collected Volume 3, p.381 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0381.pdf (this procedure describes the conversion of acetic acid into bromoacetic acid).
  2. ^ Heller, Charles E. (September 1984). Chemical Warfare in World War I: The American Experience, 1917-1918. Combat Studies Institute. Retrieved on 2007-08-02.
  1. Chemicalland properties database
  2. Environmental Health & Safety dept, Northeastern University
  3. Public health response to biological and chemical weapons, Chapter 3 Biological and Chemical agents, WHO Guidance
  4. ^  A student lab procedure for the Wittig sequence shown, only using the related methyl ester.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ethyl_bromoacetate". A list of authors is available in Wikipedia.