Bromoacetone is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the formula . It is a colorless liquid although impure samples appear yellow or even brown. It is a

lachrymatory agent Tear gas, also known as a lachrymator agent or lachrymator (), sometimes colloquially known as "mace" after the early commercial aerosol, is a chemical weapon that stimulates the nerves of the lacrimal gland in the eye to produce tears. In ad ...

and a precursor to other

Occurrence in nature

Bromoacetone is present (less than 1%) in the essential oil of a seaweed ('' Asparagopsis taxiformis'') from the vicinity of the Hawaiian Islands.

Synthesis

Bromoacetone is available commercially, sometimes stabilized with magnesium oxide. It was first described in the 19th century, attributed to N. Sokolowsky. Bromoacetone Synthesis V

Bromoacetone is prepared by combining

bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table ( halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simi ...

and

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

, with catalytic acid. As with all ketones, acetone

enol In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The t ...

izes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. If a base is present, bromoform is obtained instead, by the

haloform reaction In chemistry, the haloform reaction is a chemical reaction in which a haloform (, where X is a halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), ...

Applications

It was used in

World War I World War I (28 July 1914 11 November 1918), often abbreviated as WWI, was one of the deadliest global conflicts in history. Belligerents included much of Europe, the Russian Empire, the United States, and the Ottoman Empire, with fightin ...

as a

chemical weapon A chemical weapon (CW) is a specialized munition that uses chemicals formulated to inflict death or harm on humans. According to the Organisation for the Prohibition of Chemical Weapons (OPCW), this can be any chemical compound intended as a ...

, called BA by British and B-Stoff ('' Weisskreuz'') by Germans. Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in organic synthesis. It is, for example, the precursor to

hydroxyacetone Hydroxyacetone, also known as acetol, is the organic chemical with the formula CH3C(O)CH2OH. It consists of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone structure. ...

by reaction with aqueous sodium hydroxide.

References

{{Chemical agents Organobromides Lachrymatory agents World War I chemical weapons Ketones

Occurrence in nature

Synthesis

Applications

See also

References