m-Cresol

meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(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 and is an isomer of p-cresol and o-cresol.[3]

Not to be confused with Metacresol purple.
m-Cresol
m-cresol
3D model of m-cresol
Names
Preferred IUPAC name
3-Methylphenol
Other names
3-Cresol
m-Cresol
3-Hydroxytoluene
m-Cresylic acid
1-Hydroxy-3-methylbenzene
3-Methylbenzenol
Identifiers
3D model (JSmol)
506719
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.253
EC Number
  • 203-39-4
101411
KEGG
RTECS number
  • GO6125000
UNII
  • 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
  • Cc1cc(O)ccc1
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 miscible
Solubility in diethyl ether miscible
Vapor pressure 0.14 mmHg (20 °C)[1]
−72.02×10−6 cm3/mol
1.5398
Viscosity 6.1 cP at 40 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed.
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
Danger
H227, H301, H311, H314, H351, H370, H372, H373, H401
P201, P202, P210, P260, P264, P270, P273, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
2
0
Flash point 86 °C
Explosive limits 1.1%–? (149 °C)[1]
Lethal dose or concentration (LD, LC):
242 mg/kg (oral, rat, 1969)
2020 mg/kg (oral, rat, 1944)
828 mg/kg (oral, mouse)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (22 mg/m3) [skin][1]
REL (Recommended)
 TWA 2.3 ppm (10 mg/m3)[1]
IDLH (Immediate danger)
 250 ppm[1]
Safety data sheet (SDS) External MSDS
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).
☒N verify (what is checkY☒N ?)
Infobox references

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, toluene 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 in the presence of nickel carbonyl.[3]

Applications

m-Cresol is a precursor to numerous compounds. Important applications include:

C7H8O + C3H6 ⇌ C10H14O

Natural occurrences

m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana).[7]

m-Cresol is a constituent of tobacco smoke.[8]

m-Cresol is a component found in secretions from the ant Colobopsis saundersi during Autothysis.[9] [10]

See also

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0155". National Institute for Occupational Safety and Health (NIOSH).
  2. "Cresol (o, m, p isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 978-3527306732.
  4. Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
  5. Stroh, R.; Sydel, R.; Hahn, W. (1963). Foerst, Wilhelm (ed.). Newer Methods of Preparative Organic Chemistry, Volume 2 (1st ed.). New York: Academic Press. p. 344. ISBN 9780323150422.
  6. Asim Kumar Mukhopadhyay (2004). Industrial Chemical Cresols and Downstream Derivatives. New York: CRC Press. pp. 99–100. ISBN 9780203997413.
  7. 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
  8. Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482. PMID 21556207.
  9. Jones, T. H.; Clark, D. A.; Edwards, A. A.; Davidson, D. W.; Spande, T. F.; Snelling, Roy R. (2004). "The chemistry of exploding ants, Camponotus spp. (cylindricus complex)". Journal of Chemical Ecology. 30 (8): 1479–1492. doi:10.1023/B:JOEC.0000042063.01424.28. PMID 15537154. S2CID 23756265.
  10. Betz, Oliver (2010). "Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion". In von Byern, Janek; Grunwald, Ingo (eds.). Biological Adhesive Systems. pp. 111–152. doi:10.1007/978-3-7091-0286-2_8. ISBN 978-3-7091-0141-4.
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