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词条 M-Cresol
释义

  1. Production

  2. Applications

  3. Natural occurrences

  4. See also

  5. References

  6. External links

{{distinguish|Metacresol purple}}{{DISPLAYTITLE:m-Cresol}}{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 416907610
| Name = m-Cresol
| ImageFile = M-Kresol.svg
| ImageSize = 120px
| ImageName = m-cresol
| ImageFile1 = m-cresol-spaceFill.png
| ImageSize1 = 150px
| ImageName1 = 3D model of m-cresol
| OtherNames = 3-Hydroxytoluene
m-Cresylic acid
3-Cresol
1-Hydroxy-3-methylbenzene
| IUPACName = 3-Methylphenol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 108-39-4
| EINECS = 203-39-4
| RTECS = GO6125000
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 17231
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 298312
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB01776
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = GGO4Y809LO
| PubChem = 342
| KEGG = C01467
| Beilstein = 506719
| Gmelin = 101411
| SMILES = Cc1cc(O)ccc1
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21105871
| InChI = 1/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
| InChIKey = RLSSMJSEOOYNOY-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RLSSMJSEOOYNOY-UHFFFAOYSA-N
|Section2={{Chembox Properties
| Appearance = colorless liquid to yellowish liquid
| Formula = C7H8O
| MolarMass = 108.14 g/mol
| Density = 1.034 g/cm3, liquid at 20 °C
| Solubility = 2.35 g/100 ml at 20 °C
5.8 g/100 ml at 100 °C
| Solubility1 = fully miscible
| Solvent1 = ethanol
| Solubility2 = fully miscible
| Solvent2 = diethyl ether
| MeltingPtC = 11
| BoilingPtC = 202.8
| RefractIndex = 1.5398
| Viscosity = 184.23 cP at 20 °C
| VaporPressure = 0.14 mmHg (20°C)[1]
| MagSus = -72.02·10−6 cm3/mol
|Section7={{Chembox Hazards
| MainHazards = May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed.
| ExternalSDS = External MSDS
| FlashPt = 86 °C
| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|227|301|311|314|318|351|370|372|373|401}}
| PPhrases = {{P-phrases|201|202|210|260|264|270|273|280|281|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|307+311|308+313|310|312|314|321|322|330|361|363|370+378|403+235|405|501}}
| NFPA-H = 3
| NFPA-F = 2
| NFPA-R = 0
| NFPA-S =
| PEL = TWA 5 ppm (22 mg/m3) [skin][1]
| ExploLimits = 1.1%-? (149°C)[1]
| IDLH = 250 ppm[1]
| LD50 = 242 mg/kg (oral, rat, 1969)
2020 mg/kg (oral, rat, 1944)
828 mg/kg (oral, mouse)[2]
| REL = TWA 2.3 ppm (10 mg/m3)[1]
|Section8={{Chembox Related
| OtherFunction_label = phenols
| OtherFunction = 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]

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 examples include:

  • pesticides such as fenitrothion and fenthion.
  • synthetic vitamin E via methylation to give the 2,3,6-trimethyphenol.[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 known as secondary doping.[4]
  • preservatives in some insulins.
  • 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 {{eqm}} C10H14O

  • the synthesis of Dicresulene and Policresulen.{{Citation needed|date=April 2017}}
  • The synthesis of Toliprolol, Tolamolol & Cresatin [122-46-3].

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]

See also

  • cresol

References

1. ^1 2 3 4 {{PGCH|0155}}
2. ^{{IDLH|cresol|Cresol (o, m, p isomers)}}
3. ^1 2 {{cite encyclopedia|author=Helmut Fiege|title=Cresols and Xylenols|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=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. ^{{cite book|last1=Stroh|first1=R.|last2=Sydel|first2=R.|last3=Hahn|first3=W.|editor1-last=Foerst|editor1-first=Wilhelm|title=Newer Methods of Preparative Organic Chemistry, Volume 2|date=1963|publisher=Academic Press|location=New York|isbn=9780323150422|page=344|edition=1st|url=https://books.google.com/books?id=LG2J6i1sUAMC&pg=PA344}}
6. ^{{cite book|author=Asim Kumar Mukhopadhyay|title=Industrial Chemical Cresols and Downstream Derivatives|date=2004|publisher=CRC Press|location=New York|isbn=9780203997413|pages=99–100|url=https://books.google.com/books?id=8OT-Nj0RmmwC}}
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. ^{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482}}

External links

  • [https://www.cdc.gov/niosh/npg/npgd0155.html NIOSH Pocket Guide to Chemical Hazards] cdc.gov
  • Chemical and physical properties chemicalbook.com
{{DEFAULTSORT:Cresol, m-}}

2 : Cresols|Alkylphenols
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