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2,4,6-Trimethylaniline

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.

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

:[[Image:Chemical structure of a 1,2-diimine.png|250px|thumb|center|A substituted 1,2-diimine ligand and an idealized metal complex]]

References

References

  1. Gerald Booth. (2007). "Nitro Compounds, Aromatic". Wiley-VCH.
  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. {{doi. 10.1021/ed300243s
  3. (1999). "Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands". [[Organic Letters]].
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anilines alkyl-substituted-benzenes
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