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| {{chembox
| | This is a preview for the new '''MathML rendering mode''' (with SVG fallback), which is availble in production for registered users. |
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| | Name = '''Mesitylene'''
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| | ImageFileL1_Ref = {{chemboximage|correct|??}}
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| | ImageFileL1 = Mesitylene-2D-skeletal.png
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| | ImageSizeL1 = 120px
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| | ImageNameL1 = Mesitylene
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| | ImageFileR1 = Mesitylene-3D-vdW.png
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| | ImageSizeR1 = 120px
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| | ImageNameR1 = Mesitylene
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| | IUPACName = 1,3,5-Trimethylbenzene
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| | OtherNames = Mesitylene<br />''sym''-Trimethylbenzene
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| | Section1 = {{Chembox Identifiers
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| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| | ChemSpiderID = 7659
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| | PubChem = 7947
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| | KEGG_Ref = {{keggcite|correct|kegg}}
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| | KEGG = C14508
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| | InChI = 1/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3
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| | InChIKey = AUHZEENZYGFFBQ-UHFFFAOYAK
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| | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChI = 1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3
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| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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| | StdInChIKey = AUHZEENZYGFFBQ-UHFFFAOYSA-N
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| | CASNo_Ref = {{cascite|correct|CAS}}
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| | CASNo = 108-67-8
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| | EINECS = 203-604-4
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| | ChEBI_Ref = {{ebicite|correct|EBI}}
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| | ChEBI = 34833
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| | SMILES = Cc1cc(cc(c1)C)C
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| }}
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| | Section2 = {{Chembox Properties
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| | Formula = C<sub>9</sub>H<sub>12</sub>
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| | MolarMass = 120.19 g/mol
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| | Density = 0.8637 g/cm³ at 20 °C
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| | MeltingPt = −44.8 °C
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| | BoilingPt = 164.7 °C
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| }}
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| | Section3 = {{Chembox Structure
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| | Dipole = 0.047 [[Debye|D]] <ref>{{Cite journal | doi = 10.1016/j.atmosenv.2004.01.019| title = Proton transfer reaction rate constants between hydronium ion
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| (H<sub>3</sub>O<sup>+</sup>) and volatile organic compounds | year = 2004 | last1 = Zhao| first1 = Jun | last2 = Zhang | first2 = Renyi | journal = Atmospheric Environment | volume = 38 | issue = 14 | pages = 2177–2185 }}</ref>
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| | Section7 = {{Chembox Hazards
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| | ExternalMSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=63908&brand=FLUKA&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fsearch%3Finterface%3DAll%26term%3Dmesitylene%26lang%3Den%26region%3DUS%26focus%3Dproduct%26N%3D0%2B220003048%2B219853269%2B219853286%26mode%3Dmatch%2520partialmax Safety data from Sigma Aldrich]
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| | FlashPt = 50 °C<ref>[http://www.cdc.gov/niosh/npg/npgd0639.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref>
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| '''Mesitylene''' or '''1,3,5-trimethylbenzene''' is a derivative of [[benzene]] with three [[methyl]] [[substituent]]s symmetrically placed on the ring. Isomeric trimethylbenzenes include [[1,2,4-Trimethylbenzene|1,2,4-trimethylbenzene]] (pseudocumene) and [[1,2,3-Trimethylbenzene|1,2,3-trimethylbenzene]] (hemimellitene). All three compounds have the [[Chemical formula|formula]] C<sub>6</sub>H<sub>3</sub>(CH<sub>3</sub>)<sub>3</sub>, which is commonly abbreviated C<sub>6</sub>H<sub>3</sub>Me<sub>3</sub>. Mesitylene is a colourless liquid with sweet aromatic odor. It is a component of [[coal tar]], which is its traditional source. It is a precursor to diverse [[fine chemicals]]. The '''mesityl''' group (Mes) is a substituent with the formula C<sub>6</sub>H<sub>2</sub>Me<sub>3</sub> and is found in various other compounds.<ref name=Ullmanns/> | | If you would like use the '''MathML''' rendering mode, you need a wikipedia user account that can be registered here [[https://en.wikipedia.org/wiki/Special:UserLogin/signup]] |
| | * Only registered users will be able to execute this rendering mode. |
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| == Preparation ==
| | Registered users will be able to choose between the following three rendering modes: |
| Mesitylene is prepared by equilibration of [[xylene]] (or simple methyl [[alkylation]] of it) over solid [[acid catalyst]]:<ref name=Ullmanns>Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a13_227}}.</ref>
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| :2 C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> ⇌ C<sub>6</sub>H<sub>3</sub>(CH<sub>3</sub>)<sub>3</sub> + C<sub>6</sub>H<sub>5</sub>CH<sub>3</sub>
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| :C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> + CH<sub>3</sub>OH → C<sub>6</sub>H<sub>3</sub>(CH<sub>3</sub>)<sub>3</sub> + H<sub>2</sub>O
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| In the laboratory, it can be prepared by trimerization of [[propyne]], also requiring an [[acid catalyst]], affords a mixture of 1,3,5- and 1,2,4-trimethylbenzenes.
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| | :<math forcemathmode="mathml">E=mc^2</math> |
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| Catalyzing and [[Dehydration|dehydrating]] by [[sulfuric acid]], [[trimerization]] of [[acetone]] via [[aldol condensation]] also affords mesitylene.
| | <!--'''PNG''' (currently default in production) |
| | :<math forcemathmode="png">E=mc^2</math> |
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| == Reactions ==
| | '''source''' |
| Oxidation of mesitylene with [[nitric acid]] affords [[trimesic acid]] ( C<sub>6</sub>H<sub>3</sub>(CO<sub>2</sub>H)<sub>3</sub>). Using the milder oxidant [[manganese dioxide]], one obtains 3,5- dimethylbenzaldehyde. With metal centers it functions as a ligand, one example being ([[hapticity|η<sup>6</sup>]]-C<sub>6</sub>H<sub>3</sub>Me<sub>3</sub>)Mo(CO)<sub>3</sub>.<ref>Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J., Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999. ISBN 0-93570248-2.</ref>
| | :<math forcemathmode="source">E=mc^2</math> --> |
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| == Applications == | | <span style="color: red">Follow this [https://en.wikipedia.org/wiki/Special:Preferences#mw-prefsection-rendering link] to change your Math rendering settings.</span> You can also add a [https://en.wikipedia.org/wiki/Special:Preferences#mw-prefsection-rendering-skin Custom CSS] to force the MathML/SVG rendering or select different font families. See [https://www.mediawiki.org/wiki/Extension:Math#CSS_for_the_MathML_with_SVG_fallback_mode these examples]. |
| It is commonly used as a [[solvent]] in the laboratory. It serves as a ligand in organometallic chemistry, one example being ([[hapticity|η<sup>6</sup>]]-C<sub>6</sub>H<sub>3</sub>Me<sub>3</sub>)Mo(CO)<sub>3</sub>.
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| In the electronics industry, mesitylene has also been used as a [[photographic developer|developer]] for photopatternable [[silicone]]s due to its solvent properties.
| | ==Demos== |
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| 1,3,5-Trimethylbenzene is also a major urban [[volatile organic compound]] (VOC) which results from [[combustion]]. It plays a significant role in aerosol and [[tropospheric ozone]] formation as well as other reactions in [[atmospheric chemistry]].
| | Here are some [https://commons.wikimedia.org/w/index.php?title=Special:ListFiles/Frederic.wang demos]: |
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| The three [[aromatic]] hydrogen atoms of mesitylene are in identical chemical shift environments. Therefore, they only give a single peak near 6.8 ppm in the [[1H NMR]] spectrum. For this reason, mesitylene is sometimes used as an [[internal standard]] in NMR samples that contain aromatic protons.<ref>http://chemicalland21.com/industrialchem/organic/MESITYLENE.htm</ref>
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| == History ==
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| Mesitylene was first prepared in 1837 by [[Robert Kane (chemist)|Robert Kane]], an Irish chemist, by heating acetone with concentrated sulfuric acid.<ref>Robert Kane (1839) [http://books.google.com/books?id=AuIcAQAAMAAJ&pg=PA99#v=onepage&q&f=false "On a series of combinations derived from pyroacetic spirit] [acetone]" ''Transactions of the Royal Irish Academy'', vol. 18, pages 99–125.</ref> He named his new substance "mesitylene" because the German chemist [[Carl Reichenbach]] had named acetone "mesit" (from the Greek μεσίτης, the mediator),<ref>Reichenbach's research is excerpted in: C. Reichenbach (1834) [http://books.google.com/books?id=P0s9AAAAcAAJ&pg=PA298#v=onepage&q&f=false "Ueber Mesit (Essiggeist) und Holzgeist"] (On mesit (spirit of vinegar) and wood spirits), ''Annalen der Pharmacie'', vol. 10, no. 3, pages 298–314.</ref> and Kane believed that his reaction had dehydrated mesit, converting it to an [[alkene]], "mesitylene".<ref>For an explanation of the original of the name "mesitylene", see also: Henry E. Roscoe, ''A Treatise on Chemistry'' (New York, New York: D. Appleton and Co., 1889), vol. III, [http://books.google.com/books?id=atXNAAAAMAAJ&pg=PA102#v=onepage&q&f=false page 102], footnote 2.</ref> However, Kane's determination of the chemical composition ("empirical formula") of mesitylene was incorrect. The correct empirical formula was provided by [[August Wilhelm von Hofmann|August W. von Hofmann]] in 1849.<ref>A.W. Hofmann (1849) "On the composition of mesitilole [mesitylene], and some of its derivatives", ''The Quarterly Journal of the Chemical Society of London'', vol. 2, [http://books.google.com/books?id=oKAwAAAAYAAJ&pg=PA104#v=onepage&q&f=false pages 104–115]. (Note: The empirical formula of mesitylene as stated in Hofmann's paper ( C<sub>18</sub>H<sub>12</sub> ) is incorrect; however, this happened because Hofmann used 6 as the atomic weight of carbon, instead of the correct atomic weight of 12. Once the correct atomic weight is used in Hofmann's calculations, his results give the correct empirical formula of C<sub>9</sub>H<sub>12</sub>.)</ref> In 1866 [[Adolf von Baeyer]] showed that mesitylene's structure was consistent with that of 1,3,5-trimethylbenzene;<ref>Adolf von Baeyer (1866) [http://books.google.com/books?id=yYlKAAAAYAAJ&pg=RA1-PA297#v=onepage&q&f=false "Ueber die Condensationsproducte des Acetons"] (On condensation products of acetone), ''Annalen der Chemie und Pharmacie'', vol. 140, pages 297–306.</ref> however, conclusive proof that mesitylene was identical to 1,3,5-trimethylbenzene was provided by [[Albert Ladenburg]] in 1874.<ref>Albert Ladenburg (1874) "Ueber das Mesitylen" (On mesitylene), ''Berichte der deutschen chemischen Gesellschaft'', vol. 7, pages 1133–1137. {{DOI| 10.1002/cber.18740070261}}</ref>
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