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.^[1]

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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82545
ChemSpider	6647 Y
ECHA InfoCard	100.001.632
KEGG	C19540 Y
PubChem CID	6913
UNII	YIR5CRL5BG Y
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). Y verify (what is YN ?) Infobox references

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