2,2,6,6-Tetramethylpiperidine

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2,2,6,6-Tetramethylpiperidine
Tetramethylpiperidine.png
Names
IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine
Tetramethylpiperidine
Identifiers
Abbreviations TMP
768-66-1 YesY
ChemSpider 12493 YesY
EC number 212-199-3
Jmol-3D images Image
PubChem 13035
Properties
C9H19N
Molar mass 141.25 g·mol−1
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 R10 R22 R36/37/38
S-phrases S16 S26 S37/39
Except where noted otherwise, data is 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.

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 synthesis






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.

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]