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Wikipedia

m-Cresol

April 08, 2024

Not to be confused with Metacresol purple.

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]

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
  • 108-39-4 Y
3D model (JSmol)
  • Interactive image
506719
ChEBI
  • CHEBI:17231 N
ChEMBL
  • ChEMBL298312 N
ChemSpider
  • 21105871 N
DrugBank
  • DB01776 N
ECHA InfoCard 100.003.253
EC Number
  • 203-39-4
101411
KEGG
  • C01467
  • 342
RTECS number
  • GO6125000
UNII
  • GGO4Y809LO N
  • DTXSID6024200
  • 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:
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)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 YN ?)

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, 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 edit

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

C7H8O + C3H6 ⇌ C10H14O

Natural occurrences edit

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 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 or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b c 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.

External links edit

  • NIOSH Pocket Guide to Chemical Hazards cdc.gov
  • Chemical and physical properties chemicalbook.com

April 08, 2024
cresol, confused, with, metacresol, purple, meta, cresol, also, methylphenol, organic, compound, with, formula, ch3c6h4, colourless, viscous, liquid, that, used, intermediate, production, other, chemicals, derivative, phenol, isomer, cresol, cresol, namesprefe. Not to be confused with Metacresol purple 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 m Cresol NamesPreferred IUPAC name 3 MethylphenolOther names 3 Cresolm Cresol3 Hydroxytoluenem Cresylic acid1 Hydroxy 3 methylbenzene3 MethylbenzenolIdentifiersCAS Number 108 39 4 Y3D model JSmol Interactive imageBeilstein Reference 506719ChEBI CHEBI 17231 NChEMBL ChEMBL298312 NChemSpider 21105871 NDrugBank DB01776 NECHA InfoCard 100 003 253EC Number 203 39 4Gmelin Reference 101411KEGG C01467PubChem CID 342RTECS number GO6125000UNII GGO4Y809LO NCompTox Dashboard EPA DTXSID6024200InChI InChI 1S C7H8O c1 6 3 2 4 7 8 5 6 h2 5 8H 1H3 NKey RLSSMJSEOOYNOY UHFFFAOYSA N NInChI 1 C7H8O c1 6 3 2 4 7 8 5 6 h2 5 8H 1H3Key RLSSMJSEOOYNOY UHFFFAOYAJSMILES Cc1cc O ccc1PropertiesChemical formula C7H8OMolar mass 108 14 g molAppearance colorless liquid to yellowish liquidDensity 1 034 g cm3 liquid at 20 CMelting 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 C5 8 g 100 ml at 100 CSolubility in ethanol miscibleSolubility in diethyl ether miscibleVapor pressure 0 14 mmHg 20 C 1 Magnetic susceptibility x 72 02 10 6 cm3 molRefractive index nD 1 5398Viscosity 6 1 cP at 40 CHazardsOccupational 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 PictogramsSignal word DangerHazard statements H227 H301 H311 H314 H351 H370 H372 H373 H401Precautionary statements 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 P501NFPA 704 fire diamond 320Flash point 86 CExplosive limits 1 1 149 C 1 Lethal dose or concentration LD LC LD50 median dose 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 MSDSRelated compoundsRelated phenols o cresol p cresol phenolExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Applications 3 Natural occurrences 4 See also 5 References 6 External linksProduction editTogether 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 editm 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 dd synthesis of dicresulene and policresulen citation needed synthesis of toliprolol tolamolol amp cresatin citation needed Natural occurrences editm 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 editCresolReferences edit a b c d e NIOSH Pocket Guide to Chemical Hazards 0155 National Institute for Occupational Safety and Health NIOSH Cresol o m p isomers Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH a b c Helmut Fiege 2007 Cresols and Xylenols Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a08 025 ISBN 978 3527306732 Alan G MacDiarmid and Arthur J Epstein 1995 Secondary Doping in Polyaniline Synthetic Metals 69 85 92 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 Asim Kumar Mukhopadhyay 2004 Industrial Chemical Cresols and Downstream Derivatives New York CRC Press pp 99 100 ISBN 9780203997413 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 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 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 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 External links editNIOSH Pocket Guide to Chemical Hazards cdc gov Chemical and physical properties chemicalbook com Retrieved from https en wikipedia org w index php title M Cresol amp oldid 1194458629, wikipedia, wiki, book, books, library,

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