2,6-Dimethylpiperidine

2,6-Dimethylpiperidine
Names
	Preferred IUPAC name 2,6-Dimethylpiperidine
	Other names 2,6-Lupetidine
Identifiers
CAS Number	504-03-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	62076 ;
ECHA InfoCard	100.007.256
RTECS number	OK5775000;
CompTox Dashboard (EPA)	DTXSID8048527 ;
	InChI InChI=1S/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3 Key: SDGKUVSVPIIUCF-UHFFFAOYSA-N ; 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	113.204 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
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
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). verify (what is ?) 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

^ 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

[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

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