2,4,6-Trimethylaniline
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| Names | |||
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| IUPAC name
2,4,6-Trimethylaniline
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| Other names
Aminomesitylene; 2,4,6-Trimethylbenzenamine; Mesitylamine; Mesidine
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| Identifiers | |||
88-05-1  |
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| ChemSpider | 6647 |
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| Jmol 3D model | Interactive image | ||
| KEGG | C19540 |
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| PubChem | 6913 | ||
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| Properties | |||
| C9H13N | |||
| Molar mass | 135.21 g/mol | ||
| Density | 0.963 g/mL | ||
| Boiling point | 233 °C (451 °F; 506 K) | ||
| Vapor pressure | {{{value}}} | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,4,6-Trimethylaniline is a 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]
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File:Chemical structure of a 1,2-diimine.pngA substituted 1,2-diimine ligand and an idealized metal complex.
Condensation with 1,3-diketones gives NacNac ligands.
References
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- ↑ Gerald Booth "Nitro Compounds, Aromatic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. 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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
