Harman Patil (Editor)

Ethyl bromoacetate

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Density  1.51 g/cm³
Molar mass  167.01 g/mol
Melting point  -38 °C
Boiling point  158 °C
Formula  C4H7O2Br
Ethyl bromoacetate wwwsigmaaldrichcomcontentdamsigmaaldrichstr
Related compounds  Pepper spray Chloropicrin
Appearance  Colorless to yellow liquid

Ethyl bromoacetate


Ethyl 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. It is a lachrymator and has a fruity, pungent odor. It is also a highly toxic alkylating agent and may be fatal if inhaled.

Contents

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 odorless, toxic gases. It is listed by the World Health Organization 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.

In organic synthesis, it is a versatile alkylating agent. Its major application involves the Reformatsky 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:

References

Ethyl bromoacetate Wikipedia


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