17281-59-3

Basic information

• Product Name: N-(CYANOMETHYL)PYRIDINIUM CHLORIDE
• Synonyms: N-(CYANOMETHYL)PYRIDINIUM CHLORIDE;1-(CYANOMETHYL)PYRIDINIUM CHLORIDE;N-(Cyanomethyl)pyridinium chloride, 97+%;I-Cyanomethylpyridinium Chloride
• CAS NO: 17281-59-3
• Molecular Formula: C₇H₇N₂*Cl
• Molecular Weight: 154.6
• EINECS: 241-312-9
• Product Categories: Heterocyclic Compounds;Pyridinium Compounds;C7 and C8;Heterocyclic Building Blocks;Pyridines
• Mol File: 17281-59-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 167-170 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Water Solubility: Soluble in water
• BRN: 3728392
• CAS DataBase Reference: N-(CYANOMETHYL)PYRIDINIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(CYANOMETHYL)PYRIDINIUM CHLORIDE(17281-59-3)
• EPA Substance Registry System: N-(CYANOMETHYL)PYRIDINIUM CHLORIDE(17281-59-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 17281-59-3(Hazardous Substances Data)

Usage

Chemical Properties

beige crystalline powder

InChI:InChI=1/C7H7N2.ClH/c8-4-7-9-5-2-1-3-6-9;/h1-3,5-6H,7H2;1H/q+1;/p-1

Upstream product

• 110-86-1 pyridine 
• 107-14-2 chloroacetonitrile 

Downstream Products

• 19788-49-9 Ethyl 2-mercaptopropionate 
• 27032-01-5 pyridinium 1-dicyanomethylide 
• 623-51-8 ethyl 2-sulfanylacetate 
• 63014-89-1 2-aminoindolizine-1-carbonitrile 
• 1616370-99-0 1-(2-oxo-8-hydroxy-7-methyl-2H-chromen-3-yl)pyridinium chloride 
• 1353724-96-5 1-chloro-2-(4-nitrophenyl)indolizine-3-carbonitrile 
• 1353724-95-4 1-bromo-2-(4-nitrophenyl)indolizine-3-carbonitrile 
• 1268853-31-1 4-(4-fluorophenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile 
• 1268853-30-0 4-(3,4-dihydroxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile 
• 1268853-29-7 4-(4-hydroxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile 
• 1268853-27-5 4-(3,4-dimethoxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile 
• 1268449-62-2 3-amino-3-(4-bromobenzoyl)-4-(1-pyridinio)thiophene-5-thiolate 
• 1268449-61-1 3-amino-2-(4-chlorobenzoyl)-4-(1-pyridinio)thiophene-5-thiolate 

Relevant articles and documents

Switching the reactivity of cyanomethylpyridinium salts in the 1,3-cycloaddition conditions with alkyl propiolates to cyanoindolizines or cyanoazaindolizinyl-indolizines

A particular reactivity of 1-cyanomethylpyridinium salts was revealed in the [3 + 2] cycloaddition conditions with alkyl propiolates. Cycloadducts 3 were obtained in reactions carried out at room temperature while refluxing in CH3CN provided unexpected ethyl or methyl 3-(3-cyanoimidazo[1,2-a]pyridin-2-yl)indolizine-1-carboxylates 4. The structure of the new 2:1 azaindolizine-indolizine adducts was secured by X-ray analysis. Methodological efforts have enabled the adjustment of the reactivity towards the formation of 3-cyanoindolizines 3 or cyanoazaindolizine-indolizines 4. A mechanism for the formation of azaindolizine-indolizines was proposed. A portfolio of rare cyanoindolizines and cyanoazaindolizine-indolizines has been successfully obtained.

Synthesis of 3-aminochromenes: The Zincke reaction revisited

3-Aminocoumarines and 2-iminochromen-3-amines were efficiently prepared from the Zincke-ring-opening reaction of the corresponding 2H-chromen-3- pyridinium chlorides using N-methylpiperazine. This methodology unravels the marked potential of pyridinium salts as protective groups for primary amines. These scaffolds can be considered important building blocks for new novobiocin analogues and heterocyclic compounds.

One-pot approach to the synthesis of novel 12H-chromeno[2′,3′:4,5]imidazo[1,2-a]pyridines in aqueous media

The chromeno-imidazo[1,2-a]pyridine scaffold was generated in an one pot condensation/cyclization reaction involving a salicylaldehyde and 1-(cyanomethyl)pyridinium chloride, in aqueous sodium carbonate solution. These novel compounds were isolated in 47-71% yield. The reaction pathway was followed by 1H NMR spectroscopy allowing a clear understanding of the side reactions involved in the process. Different mono-substituted pyridinium chlorides were synthesized and reacted with mono-substituted salicylaldehydes and a detailed discussion of the scope of the synthetic method is also presented.