2,4,6-Trimethylaniline

477210899 2,4,6-Trimethylaniline.svg 150px Skeletal formula 2,4,6-Trimethylaniline-3D-balls.png 125px Ball-and-stick model 2,4,6-Trimethylaniline Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine correct CAS 88-05-1 82545 correct chemspider 6647 201-794-3 correct kegg C19540 6913 correct FDA YIR5CRL5BG 2810 (ANILINE, 2,4,6-TRIMETHYL-) 1S/C9H13N/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,10H2,1-3H3 KWVPRPSXBZNOHS-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)N)C C9H13N 135.21 g/mol 0.963 g/mL -4.9 233 2,4,6-Trimethylaniline is an organic compound with formula (CH3)3C6H2NH2. It is an aromatic amine that is of commercial interest as a precursor to dyes. It is prepared by selective nitration of mesitylene, avoiding oxidation of the methyl groups, followed by reduction of the resulting nitro group to the aniline.Gerald Booth Nitro Compounds, Aromatic Ullmann's Encyclopedia of Industrial Chemistry 2007 Wiley-VCH Weinheim 10.1002/14356007.a17_411 9783527303854 Coordination chemistry Trimethylaniline is a building block to a variety of bulky ligands. Condensation with glyoxal gives the 1,2-diimine ligands. An example is glyoxal-bis(mesitylimine), a yellow solid that is synthesized by condensation of 2,4,6-trimethylaniline and glyoxal. The diimine is a useful precursor to popular NHC ligands including IMes.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. 10.1021/ed300243s N-heterocyclic carbenes, as found in 2nd generation Grubbs' catalyst, are also prepared from this compound.Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands Scholl, M. Ding, S. Lee, C. W. Grubbs, R. H. Organic Letters 1999 1 6 953–956 10.1021/ol990909q 10823227 250px|thumb|center|A substituted 1,2-diimine ligand and an idealized metal complex References Category:Anilines Category:Mesityl compounds