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Mesitylene
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==Applications== Mesitylene is mainly used as a precursor to [[2,4,6-trimethylaniline]], a precursor to colorants. This derivative is prepared by selective mononitration of mesitylene, avoiding oxidation of the methyl groups.<ref name=Booth>{{cite encyclopedia|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411|isbn=978-3527306732}}</ref> ===Niche uses=== [[File:(Mesitylene)molybdenum tricarbonyl.png|left|thumb|150px|class=skin-invert-image|Structure of (mesitylene)molybdenum tricarbonyl, [(Ξ·<sup>6</sup>-C<sub>6</sub>H<sub>3</sub>Me<sub>3</sub>)Mo(CO)<sub>3</sub>] ]] Mesitylene is used in the laboratory as a specialty solvent. In the electronics industry, mesitylene has been used as a [[photographic developer|developer]] for photopatternable [[silicone]]s due to its solvent properties. 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|<sup>1</sup>H NMR]] spectrum; the same is also true for the nine [[methyl group|methyl]] protons, which give a singlet near 2.3 ppm. For this reason, mesitylene is sometimes used as an [[internal standard]] in NMR samples that contain aromatic protons.<ref>{{Cite web|url=http://chemicalland21.com/industrialchem/organic/MESITYLENE.htm|title=Mesitylene (1,3,5-Trimethyl Benzene)}}</ref> [[Uvitic acid]] is obtained by oxidizing mesitylene or by condensing [[pyruvic acid]] with [[Barium hydroxide|baryta water]].<ref>{{cite web|title=Definition of uvitic acid|url=http://www.merriam-webster.com/dictionary/uvitic%20acid|publisher=merriam-webster.com|accessdate=31 October 2016}}</ref> The [[Gattermann reaction]] can be simplified by replacing the HCN/AlCl<sub>3</sub> combination with [[zinc cyanide]] (Zn(CN)<sub>2</sub>).<ref name=simplfy>{{cite journal| author1 = Adams R. | last2=Levine | first2=I.| title = Simplification of the Gattermann Synthesis of Hydroxy Aldehydes| journal = [[J. Am. Chem. Soc.]]| year = 1923| volume = 45| pages = 2373β77| doi = 10.1021/ja01663a020| issue = 10| author1-link=Roger Adams }}</ref> Although it is highly toxic, Zn(CN)<sub>2</sub> is a solid, making it safer to work with than gaseous hydrogen cyanide (HCN).<ref name=Vol9>{{cite book|last1=Adams|first1=Roger|title=Organic Reactions, Volume 9|date=1957|publisher=John Wiley & Sons, Inc.|location=New York| pages = 38 & 53β54|isbn=9780471007265|doi=10.1002/0471264180.or009.02}}</ref> The Zn(CN)<sub>2</sub> reacts with the HCl to form the key HCN reactant and ZnCl<sub>2</sub> that serves as the Lewis-acid catalyst ''in-situ''. An example of the Zn(CN)<sub>2</sub> method is the synthesis of [[mesitaldehyde]] from mesitylene.<ref>{{OrgSynth| last1 =Fuson | first1=R. C. | last2=Horning |first2=E. C. |last3=Rowland |first3=S. P.|last4=Ward |first4=M. L.| title = Mesitaldehyde| collvol = 3| collvolpages = 549| year = 1955| doi=10.15227/orgsyn.023.0057}}</ref>
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