2,6-Dimethylpiperidine

2,6-Dimethylpiperidine

Names
Preferred IUPAC name 2,6-Dimethylpiperidine
Other names 2,6-Lupetidine
Identifiers
CAS Number	766-17-6 N
3D model (Jmol)	Interactive image Interactive image
ChemSpider	62076 Y
ECHA InfoCard	100.110.974
RTECS number	OK5775000
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
SMILES CC1CCCC(C)N1 N1C(C)CCCC1C
Properties
Chemical formula	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)
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	R11-R36/37/38
S-phrases	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).
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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