m-Cresol
Names IUPAC name Other names Identifiers 506719 ChEBI ChEMBL ChemSpider DrugBank ECHA InfoCard 100.003.253 EC Number 101411 KEGG RTECS number UNII 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 °C5.8 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): May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed. GHS labelling: 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) 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): TWA 5 ppm (22 mg/m3) [skin][1] TWA 2.3 ppm (10 mg/m3)[1] 250 ppm[1] Safety data sheet (SDS) External MSDS Related compounds o-cresol, p-cresol, phenol
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]
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]
m-Cresol is a precursor to numerous compounds. Important applications include:
- pesticides such as fenitrothion and fenthion
- synthetic vitamin E by methylation to give 2,3,6-trimethylphenol[3]
- antiseptics, such as amylmetacresol
- a solvent for polymers. 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.[4]
- preservatives in some insulin preparations
- the starting point in the total synthesis of thymol,[5] an important synthetic chemical for regions lacking natural sources of the flavor compound:[6]
C7H8O + C3H6 ⇌ C10H14O
- synthesis of dicresulene and policresulen[citation needed]
- synthesis of toliprolol, tolamolol & cresatin[citation needed]
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]
- Cresol
- NIOSH Pocket Guide to Chemical Hazards cdc.gov
- Chemical and physical properties chemicalbook.com
