A chlorophenol is any
organochloride
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...
of
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
that contains one or more
covalently bonded
A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
chlorine
Chlorine is a chemical element with the 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 betwee ...
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
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
chlorine
Chlorine is a chemical element with the 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 betwee ...
.
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 diss ...
, by contrast, has only one isomer because all five available ring positions on the phenol are fully chlorinated.
*
Monochlorophenol The monochlorophenols are chemical compounds consisting of phenol substituted with a chlorine atom. There are three isomers, 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol.
See also
* Chlorophenol
A chlorophenol is any organochloride of ph ...
(3 positional isomers)
**
2-Chlorophenol
**
3-Chlorophenol
**
4-Chlorophenol
*
Dichlorophenol
Dichlorophenols (DCPs) are any of several chemical compounds which are derivatives of phenol containing two chlorine atoms. There are six isomers:
* 2,3-Dichlorophenol
* 2,4-Dichlorophenol
* 2,5-Dichlorophenol
* 2,6-Dichlorophenol
2,6-Dichlo ...
(6 positional isomers)
**
2,3-Dichlorophenol
**
2,4-Dichlorophenol
**
2,5-Dichlorophenol
**
2,6-Dichlorophenol
**
3,4-Dichlorophenol
**
3,5-Dichlorophenol
*
Trichlorophenol A trichlorophenol is any organochloride of phenol that contains three covalently bonded chlorine atoms. Trichlorophenols are produced by electrophilic halogenation of phenol with chlorine. Different isomers of trichlorophenol exist according to whi ...
(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 diss ...
(1 positional isomer)
See also
*
Bromophenol
*
Iodophenol
References
{{Authority control
Chloroarenes
Phenols