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Bromoacetone is an
Bromoacetone is prepared by combining
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. The ...
with the formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
. It is a colorless liquid although impure samples appear yellow or even brown. It is a lachrymatory agent and a precursor to other 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. The ...
s.
Occurrence in nature
Bromoacetone is present (less than 1%) in theessential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
of a seaweed
Seaweed, or macroalgae, refers to thousands of species of macroscopic, multicellular, marine algae. The term includes some types of '' Rhodophyta'' (red), ''Phaeophyta'' (brown) and ''Chlorophyta'' (green) macroalgae. Seaweed species such as ...
(''Asparagopsis taxiformis
''Asparagopsis taxiformis'', (red sea plume or limu kohu) formerly ''A. sanfordiana'', is a species of red algae, with cosmopolitan distribution in tropical to warm temperate waters. Researchers have demonstrated that feeding ruminants a diet c ...
'') from the vicinity of the Hawaiian Islands
The Hawaiian Islands ( haw, Nā Mokupuni o Hawai‘i) are an archipelago of eight major islands, several atolls, and numerous smaller islets in the North Pacific Ocean, extending some from the island of Hawaii in the south to northernmost Kur ...
.
Synthesis
Bromoacetone is available commercially, sometimes stabilized withmagnesium oxide
Magnesium oxide ( Mg O), or magnesia, is a white hygroscopic solid mineral that occurs naturally as periclase and is a source of magnesium (see also oxide). It has an empirical formula of MgO and consists of a lattice of Mg2+ ions and O2− ions ...
. It was first described in the 19th century, attributed to N. Sokolowsky.
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 simila ...
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 te ...
izes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds ...
with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. If a base is present, bromoform
Bromoform (CHBr3) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, ...
is obtained instead, by the haloform reaction.
Applications
It was used inWorld 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, called BA by British and B-Stoff (''Weisskreuz
White Cross (Weiẞkreuz) is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone (BA), bromobenzyl cyanide (Camite), bromomethyl ethyl ketone (homomartonite, Bn-stoff), chloroacetone (Tonite, A-stoff), ...
'') by Germans. Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. 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.
See also
*Use of poison gas in World War I
The use of toxic chemicals as weapons dates back thousands of years, but the first large scale use of chemical weapons was during World War I. They were primarily used to demoralize, injure, and kill entrenched defenders, against whom the indisc ...
*Chloroacetone
Chloroacetone is a chemical compound with the formula . At STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It was used as a tear gas in World War I.
Synthesis
Chloroacetone may b ...
*Fluoroacetone
Fluoroacetone is an organofluorine compound with the chemical formula . In contrast to trifluoroacetone, the compound has one fluorine atom. Under normal conditions, the substance is a colorless liquid. Fluoroacetone is also a highly toxic and fl ...
*Iodoacetone
Iodoacetone is an organoiodine compound with the chemical formula The substance is a colorless liquid under normal conditions, soluble in ethanol.
Synthesis
The reaction of acetone and iodine produces iodoacetone. The reaction is typically acid ...
*Thioacetone
Thioacetone is an organosulfur compound belonging to the -thione group called thioketones, with a chemical formula (CH3)2CS. It is an unstable orange or brown substance that can be isolated only at low temperatures. Above , thioacetone readily co ...
References