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| 2,2,6,6-Tetramethylpiperidine | |
|---|---|
| IUPAC name | 2,2,6,6-Tetramethylpiperidine |
| Other names | Norpempidine Tetramethylpiperidine |
| Identifiers | |
| Abbreviations | TMP |
| CAS number | [768-66-1] |
| PubChem | |
| EINECS number | |
| SMILES | CC1(C)CCCC(C)(C)N1 |
| Properties | |
| Molecular formula | C9H19N |
| Molar mass | 141.25 g mol-1 |
| Appearance | Clear yellow 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 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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2,2,6,6-Tetramethylpiperidine or TMP or HTMP is a clear light yellow liquid with an amine odor. This amine is used in chemistry as a hindered base 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.
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