3189-57-9

Basic information

• Product Name: 1-(DICYANOMETHYLIDE)-4-METHYLPYRIDINIUM
• Synonyms: 1-(DICYANOMETHYLIDE)-4-METHYLPYRIDINIUM
• CAS NO: 3189-57-9
• Molecular Formula: C₉H₇N₃
• Molecular Weight: 157.17
• Mol File: 3189-57-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(DICYANOMETHYLIDE)-4-METHYLPYRIDINIUM(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(DICYANOMETHYLIDE)-4-METHYLPYRIDINIUM(3189-57-9)
• EPA Substance Registry System: 1-(DICYANOMETHYLIDE)-4-METHYLPYRIDINIUM(3189-57-9)

Safety Data

• Hazardous Substances Data: 3189-57-9(Hazardous Substances Data)

Upstream product

• 55602-05-6 α-thiocyanato-propionic acid ethyl ester 
• 5349-28-0 thiocyanato-acetic acid ethyl ester 

Downstream Products

• 140710-76-5 1-tert-Butyl-7-methyl-[1,3]azaphospholo[1,5-a]pyridine-3-carbonitrile 
• 140839-07-2 2-tert-Butyl-7-methyl-[1,3]azaphospholo[1,2-a]pyridine-3-carbonitrile 
• 87731-99-5 1,2-Dibenzoyl-7-methyl-indolizine-3-carbonitrile 
• 87731-94-0 (2-Benzoyl-4-methyl-indolizino[3,4,5-ab]isoindol-1-yl)-phenyl-methanone 
• 87732-03-4 9-Methyl-1,4-diphenyl-pyridazino[4,5-a]indolizine-5-carbonitrile 
• 67000-14-0 7-methyl-1,2,3-triphenyl-indolizine 
• 67000-15-1 8-methyl-1,2,3-triphenyl-6H-quinolizine-4-carbonitrile 
• 111008-09-4 3-Cyano-7-methyl-2-phenyl-indolizine-1-carboxylic acid methyl ester 

Relevant articles and documents

Preparation of New Nitrogen-Bridged Heterocycles. 42.1 Synthesis and the Reaction of Pyridinium N-Ylides Using Bifunctional Ethyl Thiocyanatoacetates

Various pyridinium (monosubstituted methylide)s were smoothly attacked to the cyano group in ethyl thiocyanatoacetate or ethyl 2-thiocyanatopropionate to afford the corresponding pyridinium (substituted cyanomethylide)s in low-to-moderate yields, while pyridinium (unsubstituted amidate)s reacted with the ester carbonyl group in the same reagents to give pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates in considerable yields. The 1,3-dipolar cycloadditions of some pyridinium (unsymmetrically substituted cyanomethylide)s with dimethyl acetylenedicarboxylate (DMAD) in various solvents afforded only dimethyl 3-cyanoindolizine-1,2-dicarboxylate, except a few examples. On the other hand, the treatment of pyridinium (thiocyanatoaceto)- or (2-thiocyanatopropiono)amidates with a strong base, such as potassium t-butoxide, gave new bicyclic mesoionic compounds, N-[2-(1,3,4-thiadiazolo(3,2-a]pyridinio)]acetamidate derivatives, in moderate yields. The intermediacy of N-[1-(2-thiocyanatopyridinio)]acetamidates in the formation reactions of the latter compounds was also proven by independent syntheses.