2,6-Dimethylpiperidine

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.

2,6-Dimethylpiperidine
Names
Preferred IUPAC name
2,6-Dimethylpiperidine
Other names
2,6-Lupetidine; nanofin; nanophyn
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.256
EC Number
  • 207-981-6
RTECS number
  • OK5775000
UNII
Properties
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)
Low
Solubility in other solvents Most organic solvents
Basicity (pKb) ca. 10
1.4394
Hazards
Main hazards Flammable
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H314, H315, H319, H335
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P332+313, P337+313, P362, P363, P370+378, P403+233
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).
N verify (what is YN ?)
Infobox references

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
  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 issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.