m-Cresol

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m-Cresol
m-cresol
3D model of m-cresol
Names
IUPAC name
3-Methylphenol
Other names
3-Hydroxytoluene
m-Cresylic acid
3-Cresol
1-Hydroxy-3-methylbenzene
Identifiers
108-39-4 YesY
ChEBI CHEBI:17231 N
ChEMBL ChEMBL298312 N
ChemSpider 21105871 N
DrugBank DB01776 N
EC Number 203-39-4
Jmol 3D model Interactive image
RTECS number GO6125000
UNII GGO4Y809LO N
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]
1.5398
Viscosity 184.23 cP at 20 °C
Hazards
Main hazards May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed.
Safety data sheet External MSDS
R-phrases R20 R24 R25 R34
S-phrases S36 S37 S39 S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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]
US health exposure limits (NIOSH):
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]
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 YesYN ?)
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.[3]

Production[edit]

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.[3][3]

Applications[edit]

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.[3] 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.[4]

m-Cresol is also used as a preservative in some insulins.

Natural occurrences[edit]

m-Cresol is a component found in temporal glands secretions during musth in male African elephants (Loxodonta africana).[5]

See also[edit]

References[edit]

  1. ^ a b c d e "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 and Health. National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ a b c d Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a08_025
  4. ^ Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92).
  5. ^ 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[edit]