Ethyl bromoacetate

Ethyl 2-bromoacetate is the chemical compound with the formula CH₂BrCO₂C₂H₅. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid^[1]

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Applications

In World War I, ethyl bromoacetate was used as a lachrymatory agent and tear gas agent for chemical warfare under the German code Weisskreuz (White Cross), and later as odorant or warning agent in odourless, toxic gases. It is listed by the WHO as a riot control agent, and was first employed for that purpose by French police in 1912. The French may have employed gas grenades of this substance in 1914 during World War I. The German army then used this attack to justify their subsequent employment of chemical weapons in 1915.^[2]

In organic synthesis, it is a versatile alkylating agent. Its major application involves the Reformatskii reaction, wherein it reacts with zinc to form a zinc enolate. The resulting BrZnCH₂CO₂Et condenses with 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 Wittig reagent (prepared by reaction with triphenylphosphine) is commonly used to prepare alpha,beta-unsaturated esters from carbonyl compounds such as benzaldehyde:^[1]

References

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.