A bromophenol is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

consisting of

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

s and

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 bonded to 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 ...

ring. They may be viewed as hydroxyl derivatives of

bromobenzene Bromobenzene is an aryl bromide and the simplest of the bromobenzenes, consisting of a benzene ring substituted with one bromine atom. Its chemical formula is . It is a colourless liquid although older samples can appear yellow. It is a reagent ...

, or as brominated derivatives of

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

. There are five basic types of bromophenols (mono- to pentabromophenol) and 19 different bromophenols in total when positional isomerism is taken into account. Bromophenols are produced by

electrophilic halogenation In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system. : A few ...

of phenol with

List of bromophenols

There is a total of 19 bromophenols, corresponding to the different ways in which bromine atoms can be attached to the five carbon atoms in the benzene ring of the phenol molecule, excluding the carbon atom to which the hydroxy group is attached. Monobromrophenols have three isomers because there is only one bromine atom that can occupy one of three ring positions on the phenol molecule; 2-bromophenol, for example, is the isomer that has a bromine atom in the '' ortho'' position. Pentabromophenol, by contrast, has only one isomer because all five available ring positions on the phenol are fully brominated. * Monobromophenol (3 positional isomers) ** 2-Bromophenol ** 3-Bromophenol ** 4-Bromophenol * Dibromophenol (6 positional isomers) ** 2,3-Dibromophenol ** 2,4-Dibromophenol ** 2,5-Dibromophenol ** 2,6-Dibromophenol ** 3,4-Dibromophenol ** 3,5-Dibromophenol * Tribromophenol (6 positional isomers) ** 2,3,4-Tribromophenol ** 2,3,5-Tribromophenol ** 2,3,6-Tribromophenol ** 2,4,5-Tribromophenol ** 2,4,6-Tribromophenol ** 3,4,5-Tribromophenol * Tetrabromophenol (3 positional isomers) ** 2,3,4,5-Tetrabromophenol ** 2,3,4,6-Tetrabromophenol ** 2,3,5,6-Tetrabromophenol * Pentabromophenol (1 positional isomer)

Health Concerns

A series of studies have shown that bromophenols derived from brominated flame retardants (BFRs) in human environments are present in human blood and breast milk. Bromophenols (as well as PBDEs) were detected in 88% of samples, with 2,4,6-Tribromophenol present in 84% of breast milk samples alone. This was widely reportedThe Independent
Researchers warn after 25 types of toxic flame retardant found in human breast milk: ‘Disturbing’
/ref> and has raised questions about restricting the use of brominated flame retardants in the future.

References

{{Authority control Bromobenzene derivatives Phenols

List of bromophenols

Health Concerns

See also

References