2,2,6,6-Tetramethylpiperidine
| 2,2,6,6-Tetramethylpiperidine | |
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2,2,6,6-Tetramethylpiperidine |
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Other names
Norpempidine |
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| Identifiers | |
| Abbreviations | TMP |
| CAS number | 768-66-1  |
| PubChem | 13035 |
| ChemSpider | 12493 |
| EC number | 212-199-3 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C9H19N |
| Molar mass | 141.25 g mol−1 |
| Appearance | Clear liquid |
| Density | 0.83 g/mL |
| Melting point |
-59 °C, 214 K, -74 °F |
| Boiling point |
152 °C, 425 K, 306 °F |
| Hazards | |
| R-phrases | R10 R22 R36/37/38 |
| S-phrases | S16 S26 S37/39 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
2,2,6,6-Tetramethylpiperidine or TMP or HTMP is a clear liquid with an amine odor. This amine is used in chemistry as a hindered base (hindered amine) because it can dissolve in organic solvents unlike ordinary 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.
[edit] See also
[edit] 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.
