Ethyl bromoacetate

Ethyl bromoacetate is listed by the World Health Organization as a riot control agent, and was first employed for that purpose by French police in 1912.

[4] The French army used rifle grenades 'grenades lacrymogènes'[5] filled with this gas against the Germans beginning in August 1914, but the weapons were largely ineffective, even though ethyl bromoacetate is twice as toxic as chlorine.

[6][a] In the early months of the war the British also used the weaponized use of tear gas agents and more toxic gasses including sulfur dioxide.

[7] The German army then used these attacks to justify their subsequent employment of it as odorant or warning agent in odorless, toxic gases and chemical weapons in 1915 under the German code Weisskreuz (White Cross).

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:[9] Organic Chemistry

Skeletal formula of ethyl bromoacetate
Skeletal formula of ethyl bromoacetate
Ball-and-stick model of ethyl bromoacetate
Ball-and-stick model of ethyl bromoacetate
NFPA 704 four-colored diamond Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas Flammability 0: Will not burn. E.g. water Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide Special hazards (white): no code
Ethyl bromoacetate as the starting point for a Wittig reaction sequence
Ethyl bromoacetate as the starting point for a Wittig reaction sequence