Jump to content

2,2,6,6-Tetramethylpiperidine

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by BG19bot (talk | contribs) at 02:11, 17 March 2016 (Remove blank line(s) between list items per WP:LISTGAP to fix an accessibility issue for users of screen readers. Do WP:GENFIXES and cleanup if needed. Discuss this at Wikipedia talk:WikiProject Accessibility#LISTGAP). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

2,2,6,6-Tetramethylpiperidine
Names
IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine
Tetramethylpiperidine
Identifiers
3D model (JSmol)
Abbreviations TMP
ChemSpider
ECHA InfoCard 100.011.090 Edit this at Wikidata
EC Number
  • 212-199-3
  • InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 checkY
    Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N checkY
  • InChI=1/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
    Key: RKMGAJGJIURJSJ-UHFFFAOYAX
  • N1C(C)(CCCC1(C)C)C
Properties
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 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)
Retrieved from "https://en.wikipedia.org/w/index.php?title=2,2,6,6-Tetramethylpiperidine&oldid=710458500"