694-55-3

Basic information

• Product Name: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE
• Synonyms: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE;1-Methyl-3-piperideine;N-Methyl-1,2,5,6-tetrahydropyridine;Pyridine, 1,2,3,6-tetrahydro-1-methyl-;1,2,3,4-tetrahydro-1-methylpyridine;1,2,3,6-Tetrahydro-1-methylpyridine;1-Methyl-1,2,5,6-tetrahydropyridine;1-Methyl-1,2,3,6-tetrahydropyridine hydrochloride,98%
• CAS NO: 694-55-3
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.16
• EINECS: 211-773-0
• Mol File: 694-55-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 198-202 °C
• Boiling Point: 115.9°Cat760mmHg
• Flash Point: 15.1°C
• Appearance: /
• Density: 0.876g/cm³
• Vapor Pressure: 6.854mmHg at 25°C
• Refractive Index: 1.47
• PKA: 9.05±0.20(Predicted)
• CAS DataBase Reference: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE(694-55-3)
• EPA Substance Registry System: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE(694-55-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 694-55-3(Hazardous Substances Data)

Usage

Chemical Properties

off-white to light beige crystalline powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1336, 1980 DOI: 10.1021/jo01295a043

InChI:InChI=1/C6H11N/c1-7-5-3-2-4-6-7/h3,5H,2,4,6H2,1H3

Upstream product

• 930-73-4 1-methyl pyridinium iodide 
• 2350-76-7 1-methylpyridinium bromide 
• 7680-73-1 N-methylpyridinium chloride 
• 33707-38-9 N-methyl-1,2-dihydropyridine 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 64-18-6 formic acid 
• 590-29-4 potassium formate 
• 445-30-7 homarine 
• 535-83-1 Trigonelline 
• 17282-40-5 N-(ethoxycarbonylmethyl)pyridinium bromide 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 50742-78-4 trans-2-benzoyl-1-methyl-3-vinylpyrrolidine 
• 50742-81-9 ((2S,3R)-1-Methyl-2-phenyl-3-vinyl-pyrrolidin-2-yl)-phenyl-methanone 
• 50742-73-9 benzoyl-(1-methyl-1,2,5,6-tetrahydropyridinio)phenylmethanide 
• 50742-70-6 benzoyl-(N-methyl-1,2,5,6-tetrahydropyridinio)methanide 
• 73657-97-3 1-methyl-2-cyano-2-piperideine 
• 50742-78-4 cis-2-benzoyl-1-methyl-3-vinylpyrrolidine 
• 73657-66-6 1-methyl-2-cyano-3-piperideine 
• 199917-93-6 N-methyl-2-methoxycarbonyl-3-ethenylpyrrolidine 

Relevant articles and documents

A convenient racemic synthesis of two isomeric tetrahydropyridyl alkaloids: Isoanatabine and anatabine

(Chemical Equation Presented) Anatabine is a major alkaloid in Nicotiana tabacum and its isomer, isoanatabine, was recently found in a marine worm. Reduction of 1-methylpyridinium iodide with sodium borohydride gave 1-methyl-3-piperideine, which was transformed with hydrogen peroxide into the N-oxide. Reaction of the N-oxide successively with trifluoroacetic anhydride and potassium cyanide gave 2-cyano-1-methyl-3-piperideine. Its reaction with 3-pyridylmagnesium chloride gave (±)-N-methyl-isoanatabine. This was transformed with m-chloroperbenzoic acid into the N-oxide which was N-demethylated with iron(II) sulfate, giving (±)-isoanatabine. The successive applications of literature procedures for the N-demethylation by decomposition of N-oxide contributed to the knowledge of the mechanism of this oxidative rearrangement. On the other hand, the reduction of 1-methylpyridinium iodide with sodium borohydride and with potassium cyanide present since the start of the reaction in a two layer ether-water system, gave 2-cyano-1-methyl-4-piperideine. This was transformed into (±)-anatabine by the same sequence of reactions used for the synthesis of (±)- isoanatabine.

trans-Dihydroxypiperidines: Synthesis, Stereochemistry, and Anti-HIV Activity

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Synthesis and pharmacological properties of 2-azabicyclooctane derivatives representing conformational restricted isopethidine analogues

The synthesis and preliminary pharmacological evaluation of the epimeric 2-methyl-6-phenyl-6-carbethoxy-2-azabicyclooctanes, representing conformationally restricted isopethidine analogues, are reported. 2-azabicyclooctanes / isopethidine analogues / structure-activity relationship