| Revision as of 14:02, 3 March 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits removed Category:Phenols; added Category:Cresols using HotCat← Previous edit |
Latest revision as of 17:35, 4 September 2024 edit undoSchubladenzieher (talk | contribs)13 editsm The initial letter in the English IUPAC nomenclature is written in lower case.Tag: Visual edit |
| (82 intermediate revisions by 54 users not shown) |
| Line 1: |
Line 1: |
|
|
{{distinguish|Metacresol purple}} |
|
{{DISPLAYTITLE:''m''-Cresol}} |
|
{{DISPLAYTITLE:''m''-Cresol}} |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 415868128 |
|
|
|
| Watchedfields = changed |
|
| Name = ''m''-Cresol |
|
|
|
| verifiedrevid = 416907610 |
|
| ImageFile = M-cresol.PNG |
|
|
|
| Name = ''m''-Cresol |
|
| ImageSize = 120px |
|
|
|
| ImageFile = M-Kresol.svg |
|
| ImageName = m-cresol |
|
|
|
| ImageSize = 120px |
|
| ImageFile1 = m-cresol-spaceFill.png |
|
|
|
| ImageName = ''m''-cresol |
|
| ImageSize1 = 150px |
|
|
| ImageName1 = 3D model of m-cresol |
|
| ImageFile1 = m-cresol-spaceFill.png |
|
|
| ImageSize1 = 150px |
|
| OtherNames = 3-Hydroxytoluene |
|
|
|
| ImageName1 = 3D model of ''m''-cresol |
|
| IUPACName = 3-Methylphenol |
|
|
|
| PIN = |
|
| Section1 = {{Chembox Identifiers |
|
|
|
| OtherNames = 3-Cresol<br/>''m''-Cresol<br />3-Hydroxytoluene<br/>''m''-Cresylic acid<br/>1-Hydroxy-3-methylbenzene<br/>3-Methylbenzenol |
|
| CASNo_Ref = {{cascite}} |
|
|
|
| IUPACName = 3-methylphenol |
|
|
| Section1 = {{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 108-39-4 |
|
| CASNo = 108-39-4 |
|
| EINECS = 203-39-4 |
|
| EINECS = 203-39-4 |
|
| RTECS = GO6125000 |
|
| RTECS = GO6125000 |
|
|
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|
| SMILES = Cc1cc(O)ccc1 |
|
|
|
| ChEBI = 17231 |
|
}} |
|
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
| Section2 = {{Chembox Properties |
|
|
|
| ChEMBL = 298312 |
|
| Appearance = colorless liquid to yellowish liquid |
|
|
|
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
|
| Formula = C<sub>7</sub>H<sub>8</sub>O |
|
|
|
| DrugBank = DB01776 |
|
| MolarMass = 108.14 g/mol |
|
|
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
| Density = 1.034 g/cm³, liquid at 20 °C |
|
|
|
| UNII = GGO4Y809LO |
|
| Solubility = 2.35 g/100 ml at 20 °C<br>5.8 g/100 ml at 100 °C |
|
|
|
| PubChem = 342 |
|
| Solubility1 = fully ] |
|
|
| Solvent1 = ethanol |
|
| KEGG = C01467 |
|
|
| Beilstein = 506719 |
|
| Solubility2 = fully ] |
|
|
| Solvent2 = diethyl ether |
|
| Gmelin = 101411 |
|
|
| SMILES = Cc1cc(O)ccc1 |
|
| MeltingPtC = 11 |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| BoilingPtC = 202.8 |
|
|
|
| ChemSpiderID = 21105871 |
|
| RefractIndex = 1.5398 |
|
|
|
| InChI = 1/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3 |
|
| Viscosity = 184.23 c] at 20 °C |
|
|
|
| InChIKey = RLSSMJSEOOYNOY-UHFFFAOYAJ |
|
}} |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
| Section7 = {{Chembox Hazards |
|
|
|
| StdInChI = 1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3 |
|
| MainHazards = May cause serious burns. Very destructive of mucous membranes. Harmful if inhaled. Toxic in contact with the skin or if swallowed. |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| ExternalMSDS = |
|
|
|
| StdInChIKey = RLSSMJSEOOYNOY-UHFFFAOYSA-N |
|
| FlashPt = 86 °C |
|
|
|
}} |
|
| RPhrases = {{R20}} {{R24}} {{R25}} {{R34}} |
|
|
|
| Section2 = {{Chembox Properties |
|
| SPhrases = {{S36}} {{S37}} {{S39}} {{S45}} |
|
|
|
| Appearance = colorless liquid to yellowish liquid |
|
| NFPA-H = 3 |
|
|
|
| Formula = C<sub>7</sub>H<sub>8</sub>O |
|
| NFPA-F = 2 |
|
|
|
| MolarMass = 108.14 g/mol |
|
| NFPA-R = 0 |
|
|
|
| Density = 1.034 g/cm<sup>3</sup>, liquid at 20 °C |
|
| NFPA-O = |
|
|
|
| Solubility = 2.35 g/100 ml at 20 °C<br>5.8 g/100 ml at 100 °C |
|
}} |
|
|
|
| Solubility1 = ] |
|
| Section8 = {{Chembox Related |
|
|
|
| Solvent1 = ethanol |
|
| Function = ]s |
|
|
|
| Solubility2 = ] |
|
| OtherFunctn = ], ], ] |
|
|
|
| Solvent2 = diethyl ether |
|
}} |
|
|
|
| MeltingPtC = 11 |
|
|
| BoilingPtC = 202.8 |
|
|
| RefractIndex = 1.5398 |
|
|
| Viscosity = 6.1 ] at 40 °C |
|
|
| VaporPressure = 0.14 mmHg (20 °C)<ref name=PGCH/> |
|
|
| MagSus = {{val|-72.02e-6|u=cm<sup>3</sup>/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 = |
|
|
| 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/m<sup>3</sup>) <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)<br/> 2020 mg/kg (oral, rat, 1944)<br/> 828 mg/kg (oral, mouse)<ref>{{IDLH|cresol|Cresol (o, m, p isomers)}}</ref> |
|
|
| REL = TWA 2.3 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/> |
|
|
}} |
|
|
| Section8 = {{Chembox Related |
|
|
| OtherFunction_label = ]s |
|
|
| OtherFunction = ], ], ] |
|
|
}} |
|
}} |
|
}} |
|
|
'''''meta''-Cresol''', also '''3-methylphenol''', is an ] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>4</sub>(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of ] and is an isomer of ] and ].<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== |
|
'''m-Cresol''', also '''3-methylphenol''', is a ], with formula (CH<sub>3</sub>)C<sub>6</sub>H<sub>4</sub>(OH). |
|
|
|
Together with many other compounds, ''m''-cresol is traditionally extracted from ], the volatile materials obtained in the production of ] from ]. This residue contains a few percent by weight of ] and isomeric ]s. In the cymene–cresol process, ] is alkylated with ] to give isomers of ], which can be oxidatively dealkylated analogous to the ]. Another method, involves ] of a mixture of ] and ] in the presence of ].<ref name=Ullmann/> |
|
|
|
|
|
|
== Applications == |
|
Amongst its uses it can be used as a solvent for dissolving polymers, most notably the conducting polymer ]. 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. |
|
|
|
''m''-Cresol is a precursor to numerous compounds. Important applications include: |
|
|
|
|
|
|
* pesticides such as ] and ] |
|
It is an isomer of ], ] and ] |
|
|
|
* synthetic ] by ] to give 2,3,6-trimethylphenol<ref name=Ullmann/> |
|
|
* ]s, such as ] |
|
|
* a ] for ]s. For example, ] 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 ] preparations |
|
|
*the starting point in the ] of ],<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> |
|
|
:: C<sub>7</sub>H<sub>8</sub>O + ] {{eqm}} ] |
|
|
*synthesis of ] and ]{{Citation needed|date=April 2017}} |
|
|
*synthesis of ], ] & ]{{cn|date=September 2022}} |
|
|
|
|
|
|
== Natural occurrences == |
|
For more information see ]. |
|
|
|
''m''-Cresol is a component found in temporal glands secretions during ] in male ]s (''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 ].<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> |
|
==References== |
|
|
|
|
|
{{Unreferenced|date =September 2007}} |
|
|
|
''m''-Cresol is a component found in secretions from the ant '']'' during ].<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 = ] | 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 = –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 == |
|
|
* ] |
|
|
|
|
|
== References == |
|
<references/> |
|
<references/> |
|
|
|
|
|
==External links == |
|
== External links == |
|
|
* cdc.gov |
|
* , aboutremediation.ca |
|
|
|
* chemicalbook.com |
|
|
|
|
|
{{DEFAULTSORT:Cresol, m-}} |
|
{{DEFAULTSORT:Cresol, m-}} |
|
|
|
|
] |
|
|
] |
|
|
] |
|
] |
|
|
] |