Bromobenzene is an aryl halide
In organic chemistry, a halogenoarene, haloarene, or aryl halide, is an organic compound in which a halogen atom is bonded to a carbon atom which is part of an aromatic ring. The haloarene are studied separately from haloalkanes because they exhibit many differences in methods of preparation and...

, C6H5Br, which can be formed by electrophilic aromatic substitution
Electrophilic aromatic substitution
Electrophilic aromatic substitution EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile...

 of benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 using bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...

. It is a clear, colourless or pale yellow liquid. It is soluble in methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

 and diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

, and very slightly soluble in cold water. The term bromobenzenes may occasionally be used to refer to a benzene containing any number of bromine atoms, or with additional substituents.


Bromobenzene is used to introduce a phenyl group via palladium-catalyzed coupling reactions
Palladium-catalyzed coupling reactions
Palladium compounds are used as a catalyst in many coupling reactions, usually as a homogeneous catalyst. Examples include:* Heck reaction between alkenes and aryl halides* Suzuki reaction between aryl halides and boronic acids...

 such as the Suzuki reaction
Suzuki reaction
The Suzuki reaction is the organic reaction of an aryl- or vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by a palladium complex. It is widely used to synthesize poly-olefins, styrenes, and substituted biphenyls, and has been extended to incorporate alkyl bromides...


Bromobenzene can be used to prepare the corresponding Grignard reagent
Grignard reaction
The Grignard reaction is an organometallic chemical reaction in which alkyl- or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is an important tool for the formation of carbon–carbon bonds...

, phenylmagnesium bromide
Phenylmagnesium bromide
Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran . Phenylmagnesium bromide is a Grignard reagent...

. This can be used, e.g. in the reaction with carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

 to prepare benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...


Bromobenzene is used as an ingredient in the manufacture of Phencyclidine
Phencyclidine , commonly initialized as PCP and known colloquially as angel dust, is a recreational dissociative drug...



It is a toxic substance and can cause liver and nervous system damage if inhaled, ingested, or absorbed through the skin.
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