Bromotoluene
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Bromotoluenes are
aryl bromide In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bro ...
s based on
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...
in which at least one aromatic hydrogen atom is replaced with a
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 ...
atom. They have the general formula C7H8–''n''Br''n'', where ''n'' = 1–5 is the number of bromine atoms.


Monobromotoluene

Monobromotoluenes are bromotoluenes containing one bromine atom. There are three isomers, each with the formula C7H7Br.


Properties

The isomers differ in the location of the bromine, but have the same chemical formula.
Benzyl bromide Benzyl bromide is an organic compound with the formula . The molecule consists of a benzene ring substituted with a bromomethyl group. It is a colorless liquid with lachrymatory properties. The compound is a reagent for introducing benzyl group ...
is an isomer, which has a bromine substituted for one of the hydrogens of
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...
's methyl group, and it is sometimes named α-bromotoluene.


Preparation

A laboratory route to ''p''-bromotoluene proceeds from ''p''-
toluidine There are three isomers of toluidine, which are organic compounds discovered and named by James Sheridan Muspratt and August Wilhelm von Hofmann in 1845. These isomers are O-Toluidine, ''o''-toluidine, ''m''-toluidine, and ''p''-toluidine, with the ...
, which is diazotiized followed by treatment with
copper(I) bromide Copper(I) bromide is the chemical compound with the formula CuBr. This white diamagnetic solid adopts a polymeric structure akin to that for zinc sulfide. The compound is widely used in the synthesis of organic compounds and as a lasing medium ...
.


Uses

Bromotoluenes are precursors to many organic building blocks. For example, the methyl group may be oxidized using
potassium permanganate Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, which dissolves in water as K+ and ions to give an intensely pink to purple solution. Potassium permanganate is widely us ...
to form the corresponding bromobenzoic acid. The methyl group may also be partially oxidized to form
bromobenzaldehyde Bromobenzaldehydes are any of three organic compounds with the formula BrC6H4COH, consisting of a formyl group and a bromine atom attached to a central benzene ring. They can be considered as aryl bromide, brominated derivatives of benzaldehyde, or ...
.


See also

*
Chlorotoluene Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–''n''Cl''n'', where ''n'' = 1–5 is the number of chlorine atoms. Monochlorotol ...
*
Iodotoluene Iodotoluenes are aryl iodides based on toluene in which at least one aromatic hydrogen atom is replaced with an iodine atom. They have the general formula C7H8–''n''I''n'', where ''n'' = 1–5 is the number of iodine atoms. Monoiodotoluene Mon ...


References

{{reflist Bromobenzene derivatives Toluenes Multiple compounds, tabular