2,2,6,6-Tetramethylpiperidine
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| Names | |
|---|---|
| IUPAC name
2,2,6,6-Tetramethylpiperidine | |
| Other names
Norpempidine Tetramethylpiperidine | |
| Identifiers | |
768-66-1  | |
| Abbreviations | TMP |
| ChemSpider | 12493 |
| EC Number | 212-199-3 |
| Jmol interactive 3D | Image |
| PubChem | 13035 |
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| Properties | |
| C9H19N | |
| Molar mass | 141.254 g/mol |
| Appearance | Clear liquid |
| Density | 0.83 g/mL |
| Melting point | −59 °C (−74 °F; 214 K) |
| Boiling point | 152 °C (306 °F; 425 K) |
| Hazards | |
| R-phrases | R10 R22 R36/37/38 |
| S-phrases | S16 S26 S37/39 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
2,2,6,6-Tetramethylpiperidine or TMP or HTMP is an organic compound of the amine class. In appearance, it is a colorless liquid and has a "fishy", amine-like odor. This amine is used in chemistry as a hindered base (hindered amine) because it can dissolve in organic solvents unlike inorganic bases such as potassium hydroxide.
There are many ways to synthesise TMP. One recent method[1] starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.
TMP is the starting material for an even stronger base lithium tetramethylpiperidide and the radical species TEMPO. Another non-nucleophilic base is N,N-diisopropylethylamine.
See also
References
- ↑ Detlef Kampmann, Georg Stuhlmüller, Roger Simon, Fabrice Cottet, Frédéric Leroux, Manfred Schlosser (2005). "A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor". Synthesis 2005 (06): 1028–1029. doi:10.1055/s-2004-834856.
External links
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