2,2,6,6-Tetramethylpiperidine

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.

2,2,6,6-Tetramethylpiperidine
Names
Preferred IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine
Tetramethylpiperidine
Identifiers
3D model (JSmol)
Abbreviations TMP
ChemSpider
ECHA InfoCard 100.011.090
EC Number
  • 212-199-3
UNII
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R-phrases (outdated) R10 R22 R36/37/38
S-phrases (outdated) S16 S26 S37/39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

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.

Preparation

Many routes for the synthesis of TMP have been reported. One 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 synthesis
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See also

References
  1. 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.
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