2,6-Dimethylpiperidine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2,6-Dimethylpiperidine
Structure of 2,6-dimethylpiperidine
Names
Preferred IUPAC name
2,6-Dimethylpiperidine
Other names
2,6-Lupetidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.110.974
RTECS number OK5775000
Properties
C7H15N
Molar mass 113.20 g·mol−1
Appearance Colorless liquid
Density 0.84 g/mL
Boiling point 113.2 °C (235.8 °F; 386.3 K)
Low
Solubility in other solvents Most organic solvents
Basicity (pKb) ca. 10
1.4394
Hazards
Main hazards Flammable
R-phrases (outdated) R11-R36/37/38
S-phrases (outdated) S16-S26
Flash point 11 °C (52 °F; 284 K)
Related compounds
Related compounds
Piperidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

2,6-Dimethylpiperidines are chemical compounds with the formula C5H8(CH3)2NH. Three stereoisomers exist: the achiral (R,S)-isomer and the chiral (R,R)/(S,S) enantiomeric pair. Dimethylpiperidines are derivatives of the heterocycle piperidine, wherein two hydrogen atoms are replaced by methyl groups.

The 2,6-dimethylpiperidines are prepared by reduction of 2,6-dimethylpyridine (2,6-lutidine). The achiral isomer is the predominant isomer produced in this reaction.

The 2,6-dimethylpiperidines are of interest for their conformational properties. The (R,S)-isomer exists largely in the chair conformation with equatorial methyl groups. The (R,R)/(S,S)-isomers are attractive chiral secondary amine building blocks.[1]

References[edit]

  1. ^ Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbuch, M.-T. and Pierre, J.-L., "Synthesis and resolution of a chiral analog of 2,2,6,6-tetramethylpiperidine and of its corresponding nitroxide", Tetrahedron Letters, 1998, volume 39, pages 2565-2568