2,2,6,6-Tetramethylpiperidine

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
2,2,6,6-Tetramethylpiperidine
150px
Names
IUPAC name
2,2,6,6-Tetramethylpiperidine
Other names
Norpempidine
Tetramethylpiperidine
Identifiers
768-66-1 YesY
Abbreviations TMP
ChemSpider 12493 YesY
EC Number 212-199-3
Jmol 3D model Interactive image
PubChem 13035
  • InChI=1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3 YesY
    Key: RKMGAJGJIURJSJ-UHFFFAOYSA-N YesY
  • 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)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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 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.

450px






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. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

Retrieved from "https://infogalactic.com/w/index.php?title=2,2,6,6-Tetramethylpiperidine&oldid=338508"