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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 (pKb) ca. 10
Refractive index (nD) 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.

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2,6-Dimethylpiperidine". A list of authors is available in Wikipedia.
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