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2,4,6-trimethylaniline
Sign in to save2,4,6-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.
Chemical data
- Formula
- C9H13N
- Molecular weight
- 135.21 g/mol
- IUPAC name
- 2,4,6-trimethylaniline
- SMILES
- CC1=CC(=C(C(=C1)C)N)C
- InChIKey
- KWVPRPSXBZNOHS-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- amine
- Mass
- 135.105
Show 4 more facts
- canonical SMILES
- CC1=CC(=C(C(=C1)C)N)C
- chemical formula
- C₉H₁₃N
- Commons category
- 2,4,6-Trimethylaniline
- melting point
- -5.0
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Coordination chemistry
- 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 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. 250px|thumb|center|A substituted 1,2-diimine ligand and an idealized metal complex
Excerpted from Wikipedia’s “2,4,6-trimethylaniline” article, available under the CC BY-SA 4.0 licence.