Chlorophenol

Last updated
Chemical structure of 2-chlorophenol 2-Chlorphenol.svg
Chemical structure of 2-chlorophenol

A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine 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. [1]

Contents

Most chlorophenols are solid at room temperature. They have a strong, medicinal taste and smell. Chlorophenols are commonly used as pesticides, herbicides, and disinfectants. [2]

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, by contrast, has only one isomer because all five available ring positions on the phenol are fully chlorinated.

See also

Related Research Articles

Monosaccharides, also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Simply, this is the structural unit of carbohydrates.

In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.

<span class="mw-page-title-main">Stereoisomerism</span> When molecules have the same atoms and bond structure but differ in 3D orientation

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<span class="mw-page-title-main">Structural formula</span> Graphic representation of a molecular structure

The structural formula of a chemical compound is a graphic representation of the molecular structure, showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bonding within the molecule is also shown, either explicitly or implicitly. Unlike other chemical formula types, which have a limited number of symbols and are capable of only limited descriptive power, structural formulas provide a more complete geometric representation of the molecular structure. For example, many chemical compounds exist in different isomeric forms, which have different enantiomeric structures but the same molecular formula. There are multiple types of ways to draw these structural formulas such as: Lewis Structures, condensed formulas, skeletal formulas, Newman projections, Cyclohexane conformations, Haworth projections, and Fischer projections.

In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

<span class="mw-page-title-main">Cyclic compound</span> Molecule with a ring of bonded atoms

A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.

<span class="mw-page-title-main">Hexachlorocyclohexane</span> Chemical compound

Hexachlorocyclohexane (HCH), C
6
H
6
Cl
6
, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. This structure has nine stereoisomers, which differ by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees.

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 which ring positions on the phenol contain chlorine atoms. 2,4,6-Trichlorophenol, for example, has two chlorine atoms in the ortho positions and one chlorine atom in the para position.

Dichlorophenols (DCPs) are any of several chemical compounds which are derivatives of phenol containing two chlorine atoms. There are six isomers:

<span class="mw-page-title-main">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism refers to the existence or possibility of isomers.

2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).

Monosaccharide nomenclature is the naming system of the building blocks of carbohydrates, the monosaccharides, which may be monomers or part of a larger polymer. Monosaccharides are subunits that cannot be further hydrolysed in to simpler units. Depending on the number of carbon atom they are further classified into trioses, tetroses, pentoses, hexoses etc., which is further classified in to aldoses and ketoses depending on the type of functional group present in them.

An iodophenol is any organoiodide of phenol that contains one or more covalently bonded iodine atoms. There are five basic types of iodophenols and 19 different iodophenols in total when positional isomerism is taken into account. Iodophenols are produced by electrophilic halogenation of phenol with iodine.

<span class="mw-page-title-main">Methylcyclohexene</span> Chemical compound

Methylcyclohexene refers to any one of three organic compounds consisting of cyclohexene with a methyl group substituent. The location of the methyl group relative to the cyclohexene double bond creates the three different structural isomers. These compounds are generally used as a reagent or intermediate to derive other organic compounds.

<span class="mw-page-title-main">3-Chlorophenol</span> Chemical compound

3-Chlorophenol is an organic compound with the molecular formula C6H4ClOH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene.

Bromochlorobenzene is any of three different positional isomers consisting of a bromine atom and a chlorine atom as substituents on a benzene ring.

In chemical nomenclature, a descriptor is a notational prefix placed before the systematic substance name, which describes the configuration or the stereochemistry of the molecule. Some listed descriptors are only of historical interest and should not be used in publications anymore as they do not correspond with the modern recommendations of the IUPAC. Stereodescriptors are often used in combination with locants to clearly identify a chemical structure unambiguously.

A bromophenol is any organobromide of phenol that contains one or more covalently bonded bromine atoms. There are five basic types of bromophenols and 19 different bromophenols in total when positional isomerism is taken into account. Bromophenols are produced by electrophilic halogenation of phenol with bromine.

A tetrachlorophenol is any organochloride of phenol that contains four covalently bonded chlorine atoms. Tetrachlorophenols are produced by electrophilic halogenation of phenol with chlorine. Different isomers of tetrachlorophenol exist according to which ring positions on the phenol contain chlorine atoms.

References

  1. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
  2. "2-Chlorophenol".