
A chlorophenol is any
organochloride
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...
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 () ...
that contains one or more
covalently bonded chlorine
Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...
atoms. There are five basic types of chlorophenols (mono- to pentachlorophenol) and 19 different chlorophenols in total when positional isomerism is taken into account. Chlorophenols are produced by
electrophilic halogenation of phenol with
chlorine
Chlorine is a chemical element; it has Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between ...
.
Most chlorophenols are solid at room temperature. They have a strong, medicinal taste and smell. Chlorophenols are commonly used as pesticides, herbicides, and disinfectants.
List of chlorophenols
There is a total of 19 chlorophenols, corresponding to the different ways in which chlorine atoms can be attached to the five carbons in the benzene ring of the phenol molecule, excluding the carbon atom to which the hydroxy group is attached.
Monochlorophenols have three isomers because there is only one chlorine atom that can occupy one of three ring positions on the phenol molecule;
2-chlorophenol, for example, is the isomer that has a chlorine atom in the ''
ortho'' position.
Pentachlorophenol
Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which disso ...
, by contrast, has only one isomer because all five available ring positions on the phenol are fully chlorinated.
*
Monochlorophenol (3 positional isomers)
**
2-Chlorophenol
**
3-Chlorophenol
**
4-Chlorophenol
4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.41.
Preparation and rea ...
*
Dichlorophenol (6 positional isomers)
**
2,3-Dichlorophenol
**
2,4-Dichlorophenol
**
2,5-Dichlorophenol
**
2,6-Dichlorophenol
**
3,4-Dichlorophenol
**
3,5-Dichlorophenol
*
Trichlorophenol (6 positional isomers)
**
2,3,4-Trichlorophenol
**
2,3,5-Trichlorophenol
**
2,3,6-Trichlorophenol
**
2,4,5-Trichlorophenol
**
2,4,6-Trichlorophenol
**
3,4,5-Trichlorophenol
*
Tetrachlorophenol (3 positional isomers)
**
2,3,4,5-Tetrachlorophenol
**
2,3,4,6-Tetrachlorophenol
**
2,3,5,6-Tetrachlorophenol
*
Pentachlorophenol
Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which disso ...
(1 positional isomer)
See also
*
Bromophenol
*
Iodophenol
References
{{Authority control
Chlorobenzene derivatives
Phenols