2,6-Dimethylpiperidine

2,6-Dimethylpiperidine
IUPAC name 2,6-Dimethylpiperidine
Other names 2,6-Lupetidine
Identifiers
CAS number	766-17-6
ChemSpider	62076 Y
RTECS number	OK5775000
Jmol-3D images	Image 1 Image 2
SMILES CC1CCCC(C)N1 N1C(C)CCCC1C
InChI InChI=1S/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3 Y Key: SDGKUVSVPIIUCF-UHFFFAOYSA-N Y InChI=1/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3 Key: SDGKUVSVPIIUCF-UHFFFAOYAU
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 (pKb)	ca. 10
Refractive index (nD)	1.4394
Hazards
R-phrases	11-36/37/38
S-phrases	16-26
Main hazards	Flammable
Flash point	53 °F
Related compounds
Related compounds	Piperidine
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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 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 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

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