M-Cresol

{{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 | PIN = | OtherNames = 3-Cresol ''m''-Cresol 3-Hydroxytoluene ''m''-Cresylic acid 1-Hydroxy-3-methylbenzene 3-Methylbenzenol | 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 = miscible | Solvent1 = ethanol | Solubility2 = miscible | Solvent2 = diethyl ether | MeltingPtC = 11 | BoilingPtC = 202.8 | RefractIndex = 1.5398 | Viscosity = 6.1 cP at 40 °C | VaporPressure = 0.14 mmHg (20 °C)<ref name=PGCH/> | MagSus = {{val|-72.02e-6|u=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 = [http://hazard.com/msds/mf/baker/baker/files/c5456.htm External MSDS] | FlashPt = 86 °C | GHSPictograms = {{GHS05}}{{GHS06}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|227|301|311|314|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 | PEL = TWA 5 ppm (22 mg/m3) [skin]<ref name=PGCH>{{PGCH|0155}}</ref> | ExploLimits = 1.1%–? (149 °C)<ref name=PGCH/> | IDLH = 250 ppm<ref name=PGCH/> | LD50 = 242 mg/kg (oral, rat, 1969) 2020 mg/kg (oral, rat, 1944) 828 mg/kg (oral, mouse)<ref>{{IDLH|cresol|Cresol (o, m, p isomers)}}</ref> | REL = TWA 2.3 ppm (10 mg/m3)<ref name=PGCH/> }} | 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.<ref name=Ullmann>{{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|isbn=978-3527306732}}</ref>

==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.<ref name=Ullmann/>

== Applications == ''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<ref name=Ullmann/> * 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.<ref>Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" ''Synthetic Metals'' 69 (85-92).</ref> *preservatives in some insulin preparations *the starting point in the total synthesis of thymol,<ref>{{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}}</ref> an important synthetic chemical for regions lacking natural sources of the flavor compound:<ref>{{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}}</ref> :: C7H8O + C3H6 {{eqm}} C10H14O *synthesis of dicresulene and policresulen{{Citation needed|date=April 2017}} *synthesis of toliprolol, tolamolol & cresatin{{cn|date=September 2022}}

== Natural occurrences == ''m''-Cresol is a component found in temporal glands secretions during musth in male African elephants (''Loxodonta africana'').<ref>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}}</ref>

''m''-Cresol is a constituent of tobacco smoke.<ref>{{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|doi-access=free}}</ref>

''m''-Cresol is a component found in secretions from the ant ''Colobopsis saundersi'' during Autothysis.<ref name=Jones>{{cite journal | last1 = Jones | first1 = T. H. | last2 = Clark | first2 = D. A. | last3 = Edwards | first3 = A. A. | last4 = Davidson | first4 = D. W. | last5 = Spande | first5 = T. F. | authorlink6 = Roy Snelling | last6 = Snelling | first6 = Roy R. | date = 2004 | title = The chemistry of exploding ants, ''Camponotus'' spp. (''cylindricus'' complex) | journal = Journal of Chemical Ecology | volume = 30 | issue = 8 | pages = 1479–1492 | doi = 10.1023/B:JOEC.0000042063.01424.28 | pmid = 15537154 | s2cid = 23756265 }}</ref><ref name=Betz>{{cite book | last = Betz | first = Oliver | date = 2010 | chapter = Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion | title = Biological Adhesive Systems | url = https://archive.org/details/biologicaladhesi00byer | url-access = limited | pages = [https://archive.org/details/biologicaladhesi00byer/page/n121 111]–152 | doi = 10.1007/978-3-7091-0286-2_8 | editor1-last = von Byern | editor1-first = Janek | editor2-last = Grunwald | editor2-first = Ingo | isbn = 978-3-7091-0141-4 }}</ref>

== See also == * Cresol

== References == <references/>

== External links == * [https://www.cdc.gov/niosh/npg/npgd0155.html NIOSH Pocket Guide to Chemical Hazards] cdc.gov * [http://www.chemicalbook.com/ChemicalProductProperty_EN_CB7852747.htm Chemical and physical properties] chemicalbook.com

{{DEFAULTSORT:Cresol, m-}} Category:Cresols Category:3-Tolyl compounds