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2,2,6,6-Tetramethylpiperidine

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2,2,6,6-Tetramethylpiperidine
Names
IUPAC name 2,2,6,6-Tetramethylpiperidine
Other names Norpempidine
Tetramethylpiperidine
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TMP
ChemSpider
ECHA InfoCard 100.011.090 Edit this at Wikidata
EC Number
  • 212-199-3
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N
  • InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3Key: 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 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 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

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

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