2,2,6,6-Tetramethylpiperidine
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| Abbreviations | TMP |
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| Molar mass | 141.254 g/mol |
| Appearance | Clear liquid |
| Density | 0.83 g/mL |
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2,2,6,6-Tetramethylpiperidine, abbreviated TMP, HTMP, or TMPH, 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). Although TMP finds limited use per se, its derivatives are a mainstay of hindered amine light stabilizers.
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. Its aqueous pKaH (conjugate acid dissociation constant, a measure of basicity) is 11.07 at 25 °C,[1] while its pKa (acid dissociation constant, a measure of acidity) is approximately 37.[2]
Preparation
Many routes for the synthesis of TMP have been reported. One method[3] starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.
See also
- 2,6-Dimethylpiperidine
- Pempidine
- TEMPO ((2,2,6,6-Tetramethylpiperidin-1-yl)oxyl)