2,2,6,6-Tetramethylpiperidine

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R-phrases (outdated) R10 R22 R36/37/38
S-phrases (outdated) S16 S26 S37/39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

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.

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[edit]

There are many ways to synthesise TMP. 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

See also[edit]

References[edit]

  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. 

External links[edit]