M-Cresol

m-Cresol
IUPAC name 3-Methylphenol
Other names 3-Hydroxytoluene
Identifiers
CAS number	108-39-4 Y
ChemSpider	21105871 N
UNII	GGO4Y809LO N
EC number	203-39-4
DrugBank	DB01776
ChEMBL	CHEMBL298312 N
RTECS number	GO6125000
Jmol-3D images	Image 1
SMILES Cc1cc(O)ccc1
InChI InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3 N Key: RLSSMJSEOOYNOY-UHFFFAOYSA-N N InChI=1/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3 Key: RLSSMJSEOOYNOY-UHFFFAOYAJ
Properties
Molecular formula	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
Solubility in water	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
Refractive index (nD)	1.5398
Viscosity	184.23 cP at 20 °C
Hazards
MSDS	External MSDS
R-phrases	R20 R24 R25 R34
S-phrases	S36 S37 S39 S45
Main hazards	May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed.
NFPA 704	2 3 0
Flash point	86 °C
Related compounds
Related phenols	o-cresol, p-cresol, phenol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.^[1]

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.^[1][1]

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.^[1] 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.^[2]

Natural occurrences

m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana).^[3]

See also

• cresol

References

1. ↑ 1.0 1.1 1.2 1.3 Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_025
2. ↑ Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
3. ↑ 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