2,4,6-Trimethylaniline
Chemical compound
From Wikipedia, the free encyclopedia
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]
| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2,4,6-Trimethylaniline | |||
| Other names
Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine | |||
| Identifiers | |||
3D model (JSmol) |
|||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.001.632 | ||
| EC Number |
| ||
| KEGG | |||
PubChem CID |
|||
| UNII | |||
| UN number | 2810 (ANILINE, 2,4,6-TRIMETHYL-) | ||
CompTox Dashboard (EPA) |
|||
| |||
| |||
| Properties | |||
| 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).
| |||
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
