My watch list

2,6-Dimethylpiperidine

2,6-Dimethylpiperidine

IUPAC name	2,6-Dimethylpiperidine
Other names	2,6-Lupetidine
Identifiers
CAS number	766-17-6
RTECS number	OK5775000
SMILES	CC1CCCC(C)N1
Properties
Molecular formula	C₇H₁₅N
Molar mass	113.20 g/mol
Appearance	Colorless liquid
Density	0.84 g/mL
Boiling point	113.2
Solubility in water	Low
Solubility in other solvents	Most organic solvents
Basicity (pK_b)	ca. 10
Refractive index (n_D)	1.4394
Hazards
Main hazards	Flammable
R-phrases	11-36/37/38
S-phrases	16-26
Flash point	53 °F
Related Compounds
Related compounds	Piperidine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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

Additional recommended knowledge

Don't let static charges disrupt your weighing accuracy

Essential Laboratory Skills Guide

Guide to balance cleaning: 8 simple steps

The 2,6-dimethylpiperidines are prepared by reduction of 2,6-dimethylpyridine (2,6-lutidine). The R,S isomer is favored.

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

^ 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

Category: Piperidines