2,4,6-Trimethylaniline

2,4,6-Trimethylaniline
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name 2,4,6-Trimethylaniline
	Other names Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine
Identifiers
CAS Number	88-05-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82545;
ChemSpider	6647 ;
ECHA InfoCard	100.001.632
KEGG	C19540 ;
PubChem CID	6913;
UNII	YIR5CRL5BG ;
CompTox Dashboard (EPA)	DTXSID5043847 ;
	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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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 mononitration of mesitylene, avoiding oxidation of the methyl groups. The resulting nitro compound is reduced 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]

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

References

Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
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
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.

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[Booth-1] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.

[Ison-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

[scholl-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.