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| verifiedrevid = 444008817 |
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|verifiedrevid = 444009999 |
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| Name = '''Mesitylene''' |
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|Name = Mesitylene |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = Mesitylene-2D-skeletal.png |
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|ImageFileL1 = 1,3,5-Trimethylbenzene.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Mesitylene |
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|ImageNameL1 = Mesitylene |
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|ImageClassL1 = skin-invert |
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| ImageFileR1 = Mesitylene-3D-vdW.png |
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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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|ImageNameR1 = Mesitylene |
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|PIN = 1,3,5-Trimethylbenzene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 139 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| IUPACName = 1,3,5-Trimethylbenzene |
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| OtherNames = Mesitylene<br />''sym''-Trimethylbenzene |
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|OtherNames = Mesitylene<ref name=iupac2013 /><br />''sym''-Trimethylbenzene |
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| Section1 = {{Chembox Identifiers |
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|Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7659 |
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|ChemSpiderID = 7659 |
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| PubChem = 7947 |
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|PubChem = 7947 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C14508 |
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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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|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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|InChIKey = AUHZEENZYGFFBQ-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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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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|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_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = AUHZEENZYGFFBQ-UHFFFAOYSA-N |
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|StdInChIKey = AUHZEENZYGFFBQ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 108-67-8 |
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|CASNo = 108-67-8 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-604-4 |
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|UNII = 887L18KQ6X |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 34833 |
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|EINECS = 203-604-4 |
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|UNNumber = 2325 |
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| SMILES = Cc1cc(cc(c1)C)C |
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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/cm<sup>3</sup> at 20 °C |
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|MeltingPtC = −44.8 |
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|BoilingPtC = 164.7 |
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|Appearance = Colorless liquid<ref name=PGCH/> |
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|Odor = Distinctive, aromatic<ref name=PGCH/> |
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|Solubility = 0.002% (20°C)<ref name=PGCH/> |
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|VaporPressure = 2 mmHg (20°C)<ref name=PGCH/> |
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|MagSus = -92.32·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3 = {{Chembox Structure |
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|Dipole = 0.047 ]<ref>{{Cite journal |doi = 10.1016/j.atmosenv.2004.01.019| title = Proton transfer reaction rate constants between hydronium ion (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 | bibcode = 2004AtmEn..38.2177Z }}</ref> |
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}} |
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|Section7 = {{Chembox Hazards |
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|ExternalSDS = |
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|FlashPtF = 122 |
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|FlashPt_ref = <ref name=PGCH>{{PGCH|0639}}</ref> |
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|IDLH = N.D.<ref name=PGCH/> |
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|REL = TWA 25 ppm (125 mg/m<sup>3</sup>)<ref name=PGCH/> |
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|PEL = none<ref name=PGCH/> |
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}} |
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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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| Section7 = {{Chembox Hazards |
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'''Mesitylene''' or '''1,3,5-trimethylbenzene''' (C<sub>9</sub>H<sub>12</sub>) is an ] with three ] ]s attached to the ] ring. It is prepared by ] of ] with ] or by trimerization of ] in sulfuric acid, which, in both cases, acts as a ] and ] agent. It is commonly used as a ] in ] and ]. It is ] and an ]; it is a low-freezing liquid. |
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'''Mesitylene''' or '''1,3,5-trimethylbenzene''' is a derivative of ] with three ] ]s positioned symmetrically around the ring. The other two isomeric ] are ] (pseudocumene) and ] (hemimellitene). All three compounds have the ] 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 colorless liquid with sweet aromatic odor. It is a component of ], which is its traditional source. It is a precursor to diverse ]s. 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/> |
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==Preparation== |
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In the electronics industry, mesitylene has also been used as a ] for photopatternable ]s due to its solvent properties. |
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Mesitylene is prepared by ] of ] over solid ]:<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>3</sub>(CH<sub>3</sub>)<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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Although impractical, it could be prepared by trimerization of ], also requiring an ], yields a mixture of 1,3,5- and 1,2,4-trimethylbenzenes. |
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1,3,5-Trimethylbenzene is also a major urban ] (VOC) which results from ]. It plays a significant role in aerosol and ] formation as well as other reactions in ]. |
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] of ] via ], which is catalyzed and ] by ] is another method of synthesizing mesitylene.<ref>{{cite book |
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The '''mesityl''' group (Mes) is a ] found as an attachment in many organic compounds. |
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|last= Cumming |
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|first= W. M. |
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|date= 1937 |
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|title= Systematic organic chemistry (3E) |
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|url= http://www.prepchem.com/synthesis-of-mesitylene/ |
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|location= New York, USA |
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|publisher= D. Van Nostrand Company |
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|page=57 |
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}}</ref> |
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==Reactions== |
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The three ] hydrogen atoms of mesitylene are in identical chemical shift environments. Therefore, they only give a single peak near 6.8 ppm in the ] spectrum. For this reason, mesitylene is sometimes used as an ] in NMR samples that contain aromatic protons.<ref>http://chemicalland21.com/industrialchem/organic/MESITYLENE.htm</ref> |
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Oxidation of mesitylene with ] yields ], C<sub>6</sub>H<sub>3</sub>(COOH)<sub>3</sub>. Using ], a milder ], 3,5-dimethyl] is formed. Mesitylene is oxidised by ] to produce ] (2,4,6-trimethylphenol).<ref>{{cite book|pages = 242–243|chapter = Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives|chapter-url = https://books.google.com/books?id=XE5VHh7uL_0C&pg=PA242|title = Fluorine in Organic Chemistry|first = Richard D.|last = Chambers|publisher = ]|year = 2004|isbn = 9780849317903}}</ref> Bromination occurs readily, giving ]:<ref>{{cite journal|journal=Org. Synth.|year=1931|volume=11|page=24|doi=10.15227/orgsyn.011.0024|title=Bromomesitylene|author=Lee Irvin Smith}}</ref> |
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:(CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>3</sub> + Br<sub>2</sub> → (CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>Br + HBr |
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Mesitylene is a ] in ], one example being the ] complex {{nowrap|]-C<sub>6</sub>H<sub>3</sub>Me<sub>3</sub>)Mo(CO)<sub>3</sub>]<ref>]; Rauchfuss, T. B. and {{ill|Robert Angelici|de|lt=Angelici, R. J.}}, Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999. {{ISBN|0-93570248-2}}.</ref>}} which can be prepared from ]. |
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==Applications== |
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Mesitylene is mainly used as a precursor to ], 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> |
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===Niche uses=== |
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]] |
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Mesitylene is used in the laboratory as a specialty solvent. In the electronics industry, mesitylene has been used as a ] for photopatternable ]s due to its solvent properties. |
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The three ] hydrogen atoms of mesitylene are in identical chemical shift environments. Therefore, they only give a single peak near 6.8 ppm in the ] spectrum; the same is also true for the nine ] protons, which give a singlet near 2.3 ppm. For this reason, mesitylene is sometimes used as an ] 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> |
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] is obtained by oxidizing mesitylene or by condensing ] with ].<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> |
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The ] can be simplified by replacing the HCN/AlCl<sub>3</sub> combination with ] (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 = ]| year = 1923| volume = 45| pages = 2373–77| 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 & 53–54|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 ] 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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==History== |
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Mesitylene was first prepared in 1837 by ], an Irish chemist, by heating acetone with concentrated sulfuric acid.<ref>Robert Kane (1839) " ''Transactions of the Royal Irish Academy'', vol. 18, pages 99–125.</ref> He named his new substance "mesitylene" because the German chemist ] had named acetone "mesit" (from the Greek μεσίτης, the mediator),<ref>Reichenbach's research is excerpted in: C. Reichenbach (1834) (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 ], "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, , footnote 2.</ref> However, Kane's determination of the chemical composition ("empirical formula") of mesitylene was incorrect. The correct empirical formula was provided by ] in 1849.<ref>A.W. Hofmann (1849) "On the composition of mesitilole , and some of its derivatives", ''The Quarterly Journal of the Chemical Society of London'', vol. 2, . (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 ] gave a correct mesitylene's empirical formula; however, with a wrong structure of tetracyclononane.<ref>Adolf von Baeyer (1866) (On condensation products of acetone), ''Annalen der Chemie und Pharmacie'', vol. 140, pages 297–306.</ref> A conclusive proof that mesitylene was trimethylbenzene was provided by ] in 1874; however, assuming wrong benzene structure of ].<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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<gallery mode="packed" heights=120 caption="Historical mesitylene structures" class="skin-invert-image"> |
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File:Mesitylen by Adolf von Baeyer.png|Mesitylene by Adolf von Baeyer (tetracyclononane) |
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File:Mesitylen by Albert Ladenburg.png|Mesitylene by Albert Ladenburg (1,2,6-trimethylprismane) |
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</gallery> |
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==Mesityl group== |
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The group (CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>- is called '''mesityl''' (organic group symbol: Mes). Mesityl derivatives, e.g. ], are typically prepared from the ] (CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>MgBr.<ref>{{cite journal|title=Isoodurene|author=Lee Irvin Smith|journal=Org. Synth.|year=1931|volume=11|page=66|doi=10.15227/orgsyn.011.0066}}</ref> Due to its large steric demand, the mesityl group is used as a large blocking group in asymmetric catalysis (to enhance diastereo- or enantioselectivity) and organometallic chemistry (to stabilize low oxidation state or low coordination number metal centers). Larger analogues with even greater steric demand, for example '''2,6-diisopropylphenyl''' (Dipp) and the analogously named '''Tripp''' ((<sup>i</sup>Pr)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>, Is) and '''supermesityl''' ((''<sup>t</sup>''Bu)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>, Mes*) groups, may be even more effective toward achieving these goals. |
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==Safety and the environment== |
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Mesitylene is also a major urban ] (VOC) which results from ]. It plays a significant role in aerosol and ] formation as well as other reactions in ].{{citation needed|date=August 2022}} |
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==References== |
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==References== |
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{{Authority control}} |
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{{Hydrocarbons}} |
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