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 Y
PubChem	13035
ChemSpider	12493 Y
EC number	212-199-3
Jmol-3D images	Image 1
SMILES N1C(C)(CCCC1(C)C)C
InChI InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 N Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N N InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 Key: RKMGAJGJIURJSJ-UHFFFAOYAX
Properties
Molecular formula	C9H19N
Molar mass	141.25 g mol−1
Appearance	Clear 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
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2,2,6,6-Tetramethylpiperidine or TMP or HTMP is a clear liquid with an amine odor. This amine is used in chemistry as a hindered base (hindered amine) because it can dissolve in organic solvents unlike ordinary 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 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

• 2,6-Dimethylpiperidine

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. 

External links

• DataSheet I
• DataSheet II
• TMP applied in synthesis in Organic Syntheses