m-Cresol
 |
|
 |
|
| Names | |
|---|---|
| IUPAC name
3-Methylphenol
|
|
| Other names
3-Hydroxytoluene
m-Cresylic acid 3-Cresol 1-Hydroxy-3-methylbenzene |
|
| Identifiers | |
108-39-4  |
|
| ChEBI | CHEBI:17231  |
| ChEMBL | ChEMBL298312 |
| ChemSpider | 21105871 |
| DrugBank | DB01776 |
| EC Number | 203-39-4 |
| Jmol 3D model | Interactive image |
| RTECS number | GO6125000 |
| UNII | GGO4Y809LO |
|
|
|
|
| Properties | |
| C7H8O | |
| Molar mass | 108.14 g/mol |
| Appearance | colorless liquid to yellowish liquid |
| Density | 1.034 g/cm3, liquid at 20 °C |
| Melting point | 11 °C (52 °F; 284 K) |
| Boiling point | 202.8 °C (397.0 °F; 475.9 K) |
| 2.35 g/100 ml at 20 °C 5.8 g/100 ml at 100 °C |
|
| Solubility in ethanol | fully miscible |
| Solubility in diethyl ether | fully miscible |
| Vapor pressure | 0.14 mmHg (20°C)[1] |
|
Refractive index (nD)
|
1.5398 |
| Viscosity | 184.23 cP at 20 °C |
| Vapor pressure | {{{value}}} |
| Related compounds | |
|
Related phenols
|
o-cresol, p-cresol, phenol |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
 verify (what is ?) |
|
| Infobox references | |
meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is an intermediate in the production of other chemicals. It is a derivative of phenol, an isomer of p-cresol and o-cresol.[2]
Production
Together with many other compounds, m-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. This residue contains a few percent by weight of phenol and isomeric cresols. In the cymene-cresol process, phenol is alkylated with propylene to give isomers of cymene, which can be oxidatively dealkylated (Hock rearrangement) analogous to the cumene process.[2][2]
Applications
m-Cresol is a precursor to the commercially important pesticides fenitrothion and fenthion. Methylation gives 2,3,6-trimethyphenol, a precursor to synthetic vitamin E.[2] it is a precursor to the antiseptic amylmetacresol.
It has been used as a solvent for dissolving polymers, e.g., polyaniline. When polyaniline is cast from a solution of m-cresol or a polyaniline film is exposed to m-cresol vapor, the conductivity is higher than a polyaniline film cast without the presence of m-cresol due to a phenomenon known as secondary doping.[3]
m-Cresol is also used as a preservative in some insulins.
Natural occurrences
m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana).[4]
See also
References
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedPGCH - ↑ 2.0 2.1 2.2 2.3 Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_025
- ↑ Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
- ↑ Some chemical constituents of the secretion from the temporal gland of the African elephant (Loxodonta africana). Jack Adams, Alexander Garcia and Christopher S. Foote, Journal Of Chemical Ecology, 1978, Volume 4, Number 1, 17-25, doi:10.1007/BF00988256
External links
- NIOSH Pocket Guide to Chemical Hazards cdc.gov
- Chemical and physical properties chemicalbook.com
- Metacresol as a biocide pesticideinfo.org
