1462-92-6

Basic information

• Product Name: 6-methyl-2,3,4,5-tetrahydropyridine
• Synonyms: 2,3,4,5-Tetrahydro-6-methylpyridine; 6-Methyl-2,3,4,5-tetrahydropyridine; pyridine, 2,3,4,5-tetrahydro-6-methyl-
• CAS NO: 1462-92-6
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.1582
• Mol File: 1462-92-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 122.8°C at 760 mmHg
• Flash Point: 19°C
• Density: 0.93g/cm³
• Vapor Pressure: 16.5mmHg at 25°C
• Refractive Index: 1.498
• PKA: 8.06±0.20(Predicted)
• CAS DataBase Reference: 6-methyl-2,3,4,5-tetrahydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-2,3,4,5-tetrahydropyridine(1462-92-6)
• EPA Substance Registry System: 6-methyl-2,3,4,5-tetrahydropyridine(1462-92-6)

Safety Data

• Hazardous Substances Data: 1462-92-6(Hazardous Substances Data)

Upstream product

• 34825-70-2 hex-5-en-1-amine 
• 109-06-8 α-picoline 
• 109-05-7 2-Methylpiperidin 
• 166303-35-1 hexa-4,5-dien-1-amine 
• 55108-01-5 1-aminohex-trans-4-ene 
• 5693-62-9 2,3,4,5-tetrahydro-6-methoxypyridine 
• 917-64-6 methyl magnesium iodide 
• 142-96-1 dibutyl ether 

Downstream Products

• 109-05-7 2-Methylpiperidin 
• 92040-47-6 N-(5-oxohexyl)benzamide 
• 109-06-8 α-picoline 
• 109240-85-9 1-(2'-iodobenzoyl)-2-methyl-1,4,5,6-tetrahydropyridine 
• 74170-66-4 2-(1,1-Dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-1-(6-methyl-3,4-dihydro-2H-pyridin-1-yl)-ethanone 
• 144882-47-3 1-(iminophenylmethyl)-3-methyl-5,6,7,8-tetrahydroindolizine 
• 108201-22-5 2-Ethoxy-9a-methyl-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin 
• 108201-16-7 5-Methyl-2,3-diphenyl-1-azabicyclo<4.3.0>non-2-en-4-on 
• 108201-31-6 6c-Methyl-1,6b-diphenyl-2-thioxo-1,2,4,5,6,6a,6b,6c-octahydrocyclopropindolizin 
• 1462-93-7 2-ethyl-3,4,5,6-tetrahydropyridine 
• 17719-74-3 1-(2-hydroxyethyl)-2-methylpiperidine 
• 24448-89-3 2-(3-hydroxypropyl)piperidine 
• 495-47-6 2-(2'-hydroxy-2'-phenylethyl)piperidine 
• 495-47-6 (±)-norsedamine 

Relevant articles and documents

Mechanism of hydrodenitrogenation on phosphides and sulfides

The mechanism of hydrodenitrogenation (HDN) of 2-methylpiperidine was studied over a silica-supported nickel phosphide catalyst (Ni 2P/SiO2, Ni/P = 1/2) and a commercial Ni-Mo-S/Al 2O3 catalyst in a three-phase trickle-bed reactor operated at 3.1 MPa and 450-600 K. Analysis of the product distribution as a function of contact time indicated that the reaction proceeded in both cases predominantly by a substitution mechanism, with a smaller contribution of an elimination mechanism. Fourier transform infrared spectroscopy (FTIR) of the 2-methylpiperidine indicated that at reaction conditions a piperidinium ion intermediate was formed on both the sulfide and the phosphide. It is concluded that the mechanism of HDN on nickel phosphide is very similar to that on sulfides. The mechanism on the nickel phosphide was also probed by comparing the reactivity of piperidine and several of its derivatives in the presence of 3000 ppm S. The relative elimination rates depended on the structure of the molecules, and followed the sequence: 4-methylpiperidine a?? piperidine > 3-methylpiperidine > 2,6-dimethylpiperidine > 2-methylpiperidine. This order of reactivity was not dependent on the number of ?±-H or ?2-H atoms in the molecules, ruling out their reaction through a single, simple mechanism. It is likely that the unhindered piperidine molecules reacted by an SN2 substitution process and the more hindered 2,6-dimethylpiperidine reacted by an E2 elimination process.

A highly reactive titanium precatalyst for intramolecular hydroamination reactions.

[reaction: see text]. Tetrakisamido titanium complexes are significantly more active than Cp2TiMe2 (1) in the intramolecular hydroamination of aminoalkynes and aminoallenes. In the latter case, the regioselectivity of the transformation depends on the nature of the precatalyst, yielding the most selective and reactive catalysis with the bis(sulfonamido) complex 11.

Palladium-Catalyzed Oxidation of Amino Alkenes to Cyclic Imines or Enamines and Amino Ketones

Amino alkenes of the type CH2=CH(CH2)nNH2 (n = 3,4) are cyclized to pyrrolines or piperideines under ''Wacker process''conditions.Amino alkenes with a secondary amino group yield the corresponding cyclic enamines, while tertiary amino alkenes give amino ketones.