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2,2,6,6-Tetramethylpiperidine



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 13035
EINECS number 212-199-3
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

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.

Additional recommended knowledge

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.

See also

References

  1. ^ A Large-Scale Low-Cost Access to the Lithium 2,2,6,6-Tetramethylpiperidide Precursor Detlef Kampmann, Georg Stuhlmüller, Roger Simon, Fabrice Cottet, Frédéric Leroux, Manfred Schlosser Synthesis 2005 1028-1029 Abstract
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2,2,6,6-Tetramethylpiperidine". A list of authors is available in Wikipedia.
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