Bromobenzenes are a group of aryl bromides/

halobenzene Halobenzenes are a group of aryl halides consisting of a benzene ring with halogen atoms as substituents. This includes these groups of halobenzenes: * Fluorobenzenes *Chlorobenzenes * Bromobenzenes *Iodobenzenes Halobenzene may also refer to any ...

s consisting of one or more

bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...

atoms as

substituent In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...

s on a

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

core. They have the formula C₆H_6–''n''Br_''n'', where ''n'' = 1–6 is the number of bromine atoms. Depending on the number of bromine substituents, there may be several

constitutional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s possible.

Isomers

* Monobromobenzene *

Dibromobenzene Dibromobenzenes are a group of bromobenzenes with the formula C6H4Br2, consisting of two bromine atoms bonded to a central benzene ring. There are three isomers of dibromobenzene: See also *Dichlorobenzene References

{{chemistry index Br ...

** 1,2-Dibromobenzene **

1,3-Dibromobenzene 1,3-Dibromobenzene (''m''-dibromobenzene) is an aryl bromide and isomer of dibromobenzene that is a colorless liquid at room temperature. Preparation 1,3-Dibromobenzene may be prepared by diazotization of 3-bromoaniline, followed by a Sandmeyer r ...

** 1,4-Dibromobenzene * Tribromobenzene ** 1,2,3-Tribromobenzene ** 1,2,4-Tribromobenzene ** 1,3,5-Tribromobenzene * Tetrabromobenzene ** 1,2,3,4-Tetrabromobenzene ** 1,2,3,5-Tetrabromobenzene ** 1,2,4,5-Tetrabromobenzene * Pentabromobenzene * Hexabromobenzene

Preparation

Bromobenzenes may be prepared by electrophilic aromatic bromination of

and benzene derivatives, using elemental

and the

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...

catalyst

iron(III) bromide Iron(III) bromide is the chemical compound with the formula FeBr3. Also known as ferric bromide, this red-brown odorless compound is used as a Lewis acid catalyst in the halogenation of aromatic compounds. It dissolves in water to give acidic s ...

. They may also be prepared from

diazonium compound Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compou ...

Reactions

Bromobenzenes may be

carboxylated Carboxylation is a chemical reaction in which a carboxylic acid is produced by treating a substrate with carbon dioxide. The opposite reaction is decarboxylation. In chemistry, the term carbonation is sometimes used synonymously with carboxylation ...

into

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...

s using

carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

. The reaction takes place in a two-phase mixture of ''p''-xylene and water as solvent, in the presence of catalytic and

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a l ...

(), tetrabutylammonium iodide (TBAI) as a

phase-transfer catalyst In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the Phase transition, transition of a reactant from one phase (matter), phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of cat ...

, and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

as a base. Below is an example reaction of 1,3-dibromobenzene to

isophthalic acid Isophthalic acid is an organic compound with the formula C6H4(CO2H)2. This colorless solid is an isomer of phthalic acid and terephthalic acid. The main industrial uses of purified isophthalic acid (PIA) are for the production of polyethylene ...

. :

References

{{reflist