2,4,6-Trimethylaniline Explained

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.^[1]

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.^[2] N-heterocyclic carbenes, as found in 2nd generation Grubbs' catalyst, are also prepared from this compound.^[3]

Notes and References

1. Encyclopedia: Gerald Booth. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry. 2007. Wiley-VCH. Weinheim. 10.1002/14356007.a17_411. 9783527303854 .
2. 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.
3. 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. . . 1999. 1 . 6. 953–956. 10.1021/ol990909q. 10823227 .