2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine
Names

Preferred IUPAC name 2,2,6,6-Tetramethylpiperidine
Other names Norpempidine Tetramethylpiperidine
Identifiers
CAS Number	768-66-1^Y
3D model (Jmol)	Interactive image
Abbreviations	TMP
ChemSpider	12493^Y
ECHA InfoCard	100.011.090
EC Number	212-199-3
PubChem	13035
InChI InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3^Y Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N^Y InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 Key: RKMGAJGJIURJSJ-UHFFFAOYAX
SMILES N1C(C)(CCCC1(C)C)C
Properties
Chemical formula	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	R10 R22 R36/37/38
S-phrases	S16 S26 S37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
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 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.

References

↑ 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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