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2,4,6-Trimethylaniline

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2,4,6-Trimethylaniline
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name 2,4,6-Trimethylaniline
Other names Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.632 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • CC1=CC(=C(C(=C1)C)N)C
Properties
Chemical formula C9H13N
Molar mass 135.21 g/mol
Density 0.963 g/mL
Melting point −4.9 °C (23.2 °F; 268.2 K)
Boiling point 233 °C (451 °F; 506 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

A substituted 1,2-diimine ligand and an idealized metal complex

References

  1. Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 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. doi:10.1021/ed300243s
  3. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. (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. 1 (6): 953–956. doi:10.1021/ol990909q. PMID 10823227.
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