| Revision as of 17:02, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473857047 of page 2,4,6-Trimethylaniline for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:22, 10 July 2024 edit Michael D. Turnbull (talk | contribs)Extended confirmed users13,722 edits Undid revision 1233168678 by 2.101.54.127 (talk) WP:BANREVERTTag: Undo |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443782393 |
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| verifiedrevid = 477210899 |
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| ImageFileL1 = Trimethylaniline.png |
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| ImageFileL1 = 2,4,6-Trimethylaniline.svg |
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| ImageSizeL1 = 115px |
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| ImageSizeL1 = 150px |
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| ImageNameL1 = Skeletal formula |
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| ImageNameL1 = Skeletal formula |
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| ImageFileR1 = 2,4,6-Trimethylaniline-3D-balls.png |
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| ImageFileR1 = 2,4,6-Trimethylaniline-3D-balls.png |
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| ImageSizeR1 = 125px |
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| ImageSizeR1 = 125px |
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| ImageNameR1 = Ball-and-stick model |
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| ImageNameR1 = Ball-and-stick model |
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| IUPACName = 2,4,6-Trimethylaniline |
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| PIN = 2,4,6-Trimethylaniline |
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| OtherNames = Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine |
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| OtherNames = Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI=82545 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6647 |
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| ChemSpiderID = 6647 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=88-05-1 |
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| CASNo=88-05-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=6913 |
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| UNII = YIR5CRL5BG |
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| SMILES=CC1=CC(=C(C(=C1)C)N)C |
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| PubChem=6913 |
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| SMILES=CC1=CC(=C(C(=C1)C)N)C |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19540 |
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| KEGG = C19540 |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>9</sub>H<sub>13</sub>N |
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| Formula=C<sub>9</sub>H<sub>13</sub>N |
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| MolarMass=135.21 g/mol |
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| MolarMass=135.21 g/mol |
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| Appearance= |
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| Appearance= |
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| Density=0.963 g/mL |
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| Density=0.963 g/mL |
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| MeltingPtC= -4.9 |
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| MeltingPt= |
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| BoilingPtC=233 |
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| BoilingPtC=233 |
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| Solubility= |
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| Solubility= |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards= |
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| FlashPt= |
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| FlashPt= |
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| AutoignitionPt = |
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| Autoignition= |
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'''2,4,6-Trimethylaniline''' is an ] with formula (CH<sub>3</sub>)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>NH<sub>2</sub>. It is an ] that is of commercial interest as a precursor to dyes. It is prepared by selective ] of ], avoiding oxidation of the methyl groups, followed by reduction of the resulting nitro group to the ].<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=9783527303854 }}</ref> |
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==Coordination chemistry== |
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Trimethylaniline is a building block to a variety of bulky ligands. Condensation with glyoxal gives the 1,2-]s. An example is ], a yellow solid that is synthesized by condensation of 2,4,6-trimethylaniline and ]. The diimine is a useful precursor to popular NHC ligands including ].<ref name=Ison>Elon A. Ison, Ana Ison "Synthesis of Well-Defined Copper N-Heterocyclic Carbene Complexes and Their Use as Catalysts for a “Click Reaction”: A Multistep Experiment That Emphasizes the Role of Catalysis in Green Chemistry" J. Chem. Educ., 2012, volume 89, pp 1575–1577. {{doi|10.1021/ed300243s}}</ref> N-heterocyclic carbenes, as found in 2nd generation ], are also prepared from this compound.<ref name=scholl>{{cite journal|title=Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands|author1=Scholl, M. |author2=Ding, S. |author3=Lee, C. W. |author4=Grubbs, R. H. |journal=] |year=1999| volume=1 |issue=6| pages=953–956| doi=10.1021/ol990909q|pmid=10823227 }}</ref> |
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:] |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Trimethylaniline}} |
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] |
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] |