766-17-6

Basic information

• Product Name: cis-2,6-Dimethylpiperidine
• Synonyms: Piperidine,2,6-dimethyl-,(2R,6S)-rel-;CIS-2,6-DIMETHYLPIPERIDINE;CIS-2,6-LUPETIDINE;CIS-LUPETIDINE;CIS-HEXAHYDRO-2,6-LUTIDINE;2,6-DIMETHYLPIPERIDINE, CIS;2,6-Dimethylpiperidine,predominantlycis,99%;cis-2,6-dimetylopiperidine
• CAS NO: 766-17-6
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.2
• EINECS: 207-981-6
• Product Categories: Pharmaceutical Intermediates
• Mol File: 766-17-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: -20℃
• Boiling Point: 127-128 °C768 mm Hg(lit.)
• Flash Point: 53 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.84 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4394(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1:11.07(+1) (25°C)
• CAS DataBase Reference: cis-2,6-Dimethylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2,6-Dimethylpiperidine(766-17-6)
• EPA Substance Registry System: cis-2,6-Dimethylpiperidine(766-17-6)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: OK5775000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 766-17-6(Hazardous Substances Data)

Usage

General Description

Cis-2,6-Dimethylpiperidine is an organic compound with a chemical formula C8H17N. It is a saturated heterocyclic compound which belongs to the class of piperidines, comprising of a piperidine ring, incorporated with two methyl groups at the 2nd and the 6th positions. The term "cis" in its name denotes that these two methyl groups are on the same side of the ring. This chemical is typically utilized in research or industrial applications such as in the production of specific pharmaceutical or chemical products. Its properties can vary under different conditions and it should be handled carefully due to its potential reactivity.

InChI:InChI=1/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3

Upstream product

• 38227-84-8 Li(cis-2,6-dimethylpiperidine(-1H)) 
• 108-18-9 diisopropylamine 
• 2439-13-6 cis-1,2,6-trimethylpiperidine 

Downstream Products

• 1027220-19-4 3-{4-[4-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-butyl]-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl}-benzonitrile 
• 244621-33-8 4-[5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl]-2-(3-cyanophenyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one 
• 1026621-81-7 3-{4-[6-((2S,6R)-2,6-Dimethyl-piperidin-1-yl)-hexyl]-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl}-benzonitrile 
• 63645-10-3 cis-2,6-dimethyl-α,α-diphenyl-1-piperidinebutanol methanesulfonate salt 
• 930117-87-6 methyl (2R)-2-acetylamino-3-(4-{[(2R,6S)-2,6-dimethylpiperidin-1-yl]methyl}phenyl)propanoate 
• 1125598-06-2 methyl 4-[2-(1-benzhydryl-5-chloro-2-{2-[({2-[(2R,6S)-2,6-dimethyl-1-piperidinyl]ethyl}sulfonyl)amino]ethyl}-1H-indol-3-yl)ethoxy]benzoate 
• 1207731-47-2 C₁₉H₂₉ClN₂O₂S 
• 887932-26-5 C₂₁H₃₀N₄O₂ 

Relevant articles and documents

Quenching of singlet oxygen by tertiary aliphatic amines. Structural effects on rates and products

A kinetic and product study of the reaction of a series of α-methyl-substituted N-methylpiperidines with thermally generated 1O2 in MeCN was carried out. It was found that as the number of α-methyl groups (Me in α-position relative to the N-atom) increases, the rate of 1O2 quenching (physical plus chemical) slightly decreases. This finding shows that, with respect to the reaction rate, steric effects are much more important than electronic effects as the latter should have produced the opposite result. The opposite outcome was instead found for the chemical quenching that leads to the N-demethylation products and N-formyl derivatives. The same trend was observed for the ratio between N-demethylation and formation of the N-formyl derivatives (NH/NCHO ratio). All these results are consistent with the mechanism reported in Scheme 1 where an exciplex is first formed that by a H-atom transfer process produces an α-amino-substituted C-radical. The latter forms the product of N-demethylation by one electron oxidation, or affords the N-formyl derivative by radical coupling (Scheme 1). Similar results were obtained with N,N-dimethylcyclohexanamine. However, this 'acyclic' amine exhibited behaviors quite distinct from those of the N-methylpiperidines series, with respect to reaction rate, extent of chemical quenching, and NH/NCHO ratio.

LITHIUM DIALKYLAMIDES. 13C PARAMETERS AND SLOW PROTON TRANSFER

The changes in 13C chemical shifts for the structural change R2NH -> R2N-Li have been measured for a series of dialkylamines.These lithiation shifts are largest at the alpha carbon (3.7-9.7 ppm) and decrease in the order α > β > χ > δ.The rates of lithium-hydrogen interchange between R2NH and R'2N-Li have been determined.The activation energies are large (9 - 17 kcal/mole) and increase as the size of R or R' increases.The slow exchange permits the direct measurement of acidity differences between pairs of amines using 13C nmr.