''meta''-Cresol, also 3-methylphenol, 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 ...
with the formula CH
3C
6H
4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative 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 () ...
and is an isomer of
''p''-cresol and
''o''-cresol.
Production
Together with many other compounds, ''m''-cresol is traditionally extracted from
coal tar
Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoria ...
, the volatile materials obtained in the production of
coke from
(bituminous) coal. This residue contains a few percent by weight 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 () ...
and isomeric
cresol
Cresols (also known as hydroxytoluene, toluenol, benzol or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also c ...
s. In the cymene–cresol process,
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 ...
is alkylated with
propylene to give isomers of
cymene, which can be oxidatively dealkylated analogous to the
cumene process. Another method, involves
carbonylation of a mixture of
methallyl chloride and
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
in the presence of
nickel carbonyl.
[
]
Applications
''m''-Cresol is a precursor to numerous compounds. Important applications include:
* pesticides such as fenitrothion and fenthion
* synthetic vitamin E
Vitamin E is a group of eight compounds related in molecular structure that includes four tocopherols and four tocotrienols. The tocopherols function as fat-soluble antioxidants which may help protect cell membranes from reactive oxygen speci ...
by methylation to give 2,3,6-trimethylphenol[
* ]antiseptic
An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...
s, such as amylmetacresol
* a solvent
A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
for polymer
A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
s. For example, polyaniline is cast from a solution of ''m''-cresol to form a polyaniline film with a superior conductivity than polyaniline alone. This phenomenon is known as secondary doping.
*preservatives in some insulin
Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the insulin (''INS)'' gene. It is the main Anabolism, anabolic hormone of the body. It regulates the metabol ...
preparations
*the starting point in the total synthesis
Total synthesis, a specialized area within organic chemistry, focuses on constructing complex organic compounds, especially those found in nature, using laboratory methods. It often involves synthesizing natural products from basic, commercially ...
of thymol, an important synthetic chemical for regions lacking natural sources of the flavor compound:
:: C7H8O + C3H6 C10H14O
*synthesis of dicresulene and policresulen
*synthesis of toliprolol, tolamolol & cresatin
Natural occurrences
''m''-Cresol is a component found in temporal glands secretions during musth
Musth or must (from Persian, ) is a periodic condition in bull (male) elephants characterized by aggressive behavior in animals, aggressive behavior and accompanied by a large rise in reproductive hormones. It has been known in Asian elephan ...
in male African elephants (''Loxodonta africana'').
''m''-Cresol is a constituent of tobacco smoke.
See also
* Cresol
Cresols (also known as hydroxytoluene, toluenol, benzol or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also c ...
References
External links
NIOSH Pocket Guide to Chemical Hazards
cdc.gov
chemicalbook.com
{{DEFAULTSORT:Cresol, m-
Cresols
3-Tolyl compounds