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
Structure of 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
  • InChI=1S/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3 checkY
    Key: SDGKUVSVPIIUCF-UHFFFAOYSA-N checkY
  • InChI=1/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3
    Key: SDGKUVSVPIIUCF-UHFFFAOYAU
  • CC1CCCC(C)N1
  • N1C(C)CCCC1C
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
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H225, H314, H315, H319, H335
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
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 checkY☒N ?)
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

See also

Compound Summary 2,6-Dimethylpiperidine on National Library of Medicine National Center

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