32081-57-5

Basic information

• Product Name: 2-Pyridineacetonitrile, a-methyl-
• Synonyms: 2-(pyridine-2-yl)propanenitrile;2-(2-pyridyl)-propionitrile;2-pyridin-2-yl-propionitrile;2-(2-Pyridyl)-propionitril;(+/-)-2-(2-Pyridyl)-propionnitril;2-(2-pyridinyl)-propanenitrile
• CAS NO: 32081-57-5
• Molecular Formula: C8H8N2
• Molecular Weight: 132.165
• Mol File: 32081-57-5.mol

Chemical Properties

• CAS DataBase Reference: 2-Pyridineacetonitrile, a-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridineacetonitrile, a-methyl-(32081-57-5)
• EPA Substance Registry System: 2-Pyridineacetonitrile, a-methyl-(32081-57-5)

Safety Data

• Hazardous Substances Data: 32081-57-5(Hazardous Substances Data)

Upstream product

• 109-04-6 2-bromo-pyridine 
• 107-12-0 propiononitrile 
• 1071002-12-4 Phosphoric acid cyano-methyl-pyridin-2-yl-methyl ester diethyl ester 
• 100-69-6 2-vinylpyridine 
• 67-56-1 methanol 
• 2739-97-1 pyridine-2-acetonitrile 
• 74-88-4 methyl iodide 
• 1122-62-9 2-acetylpyridine 
• 143-33-9 sodium cyanide 

Downstream Products

• 1122-62-9 2-acetylpyridine 

Relevant articles and documents

Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid

Hydrocyanation in the absence of toxic HCN gas is highly desirable. Addressing that challenge, transition-metal-catalyzed transfer hydrocyanation using safe HCN precursors has been developed, but these reagents generally require a Lewis acid for activation, and the control of regioselectivity often remains problematic. In this Letter, a Ni-catalyzed highly Markovnikov-selective transfer hydrocyanation that operates in the absence of any Lewis acid is reported. The readily prepared pro-aromatic 1-isopropylcyclohexa-2,5-diene-1-carbonitrile is used as the HCN source, and the reaction shows a broad substrate scope and high functional group tolerance. Terminal styrene derivatives, dienes, and internal alkynes are converted with good to excellent selectivities. Mechanistic studies provide insights into the origin of the regioselectivity.

Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis

A general and chemoselective catalytic alkylation of nitriles using a homogeneous nonprecious manganese catalyst is presented. This alkylation reaction uses naturally abundant alcohols and readily available nitriles as coupling partners. The reaction tolerates a wide range of functional groups and heterocyclic moieties, efficiently providing useful cyanoalkylated products with water as the only side product. Importantly, methanol can be used as a C1 source and the chemoselective C-methylation of nitriles is achieved. The mechanistic investigations support the multiple role of the metal-ligand manganese catalyst, the dehydrogenative activation of the alcohol, α-C-H activation of the nitrile, and hydrogenation of the in-situ-formed unsaturated intermediate.

Lithium naphthalenide-induced reductive alkylation and addition of aryl-and heteroaryl-substituted dialkylacetonitriles

Lithium naphthalenide (LN)-induced reductive alkylation/addition reactions of aryl-, pyridyl-, and 2-thienyl-substituted dialkylacetonitriles have been investigated. Upon treatment with LN in THF at -40°C, both aryl and pyridyl precursors could undergo the reductive decyanation smoothly, and the in situ generated carbanions could be readily trapped by alkyl halides, ketones, aldehydes, or even oxygen to afford a wide range of functionalized aromatic derivatives bearing a newly established quaternary carbon. To effect the desired reductive alkylation of 2-thienyldialkylacetonitriles, a much lower temperature such as -100°C was required. Also with these substrates, an interesting ring-opening/S-alkylation process was observed when the reductive alkylation were performed at -78°C to give 1-alkylsulfanyl-1,3,4-trienes. A mechanistic discussion is given for this observation.

Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof

The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particularly, savory (the “umami” taste of monosodium glutamate) or sweet taste modifiers,—savory or sweet flavoring agents and savory or sweet flavor enhancers, for food, beverages, and other comestible or orally administered medicinal products or compositions.

ANTIPARASITIC TERPENE ALKALOIDS

The present invention relates to novel terpene alkaloids and their use as antiparasitic agents. The present invention also relates to an antiparasitic agent which comprises a terpene alkaloid compound of this invention as an effective ingredient in an antiparasitic formulation. More particularly, the present invention relates to derivatives of the terpene alkaloid (1S,2R,4aS,5R,8R,8aR)-2-(acetyloxy)-8a-hydroxy-3,8-dimethyl-5-(1-methylethenyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate. Pharmaceutical compositions comprising the same are also disclosed.

Cyano Phosphate: An Efficient Intermediate for the Chemoselective Conversion of Carbonyl Compounds to Nitriles

Cyanohydrin diethyl phosphates, readily obtained from various ketones and aldehydes by reaction with diethyl phosphorocyanidate and lithium cyanide, reacted chemoselectively with samarium(II) iodide in THF to give the corresponding nitriles in excellent yields.This method was also found applicable to α,β-unsaturated carbonyl compounds via cyano phosphates to give β,γ-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds.

CYANOPHOSPHATE: AN EFFICIENT INTERMEDIATE FOR CONVERSION OF CARBONYL COMPOUNDS TO NITRILES

A novel and high yield conversion of saturated or unsaturated carbonyl compounds to nitriles via cyanophosphates by samarium diiodide in the presence of tert-butanol is described.

A New Synthesis of Aryl Hetaryl Ketones via SRN1 Reaction of Halogenated Heterocycles withPotassiophenylacetonitrile Followed by Phase-Transfer Catalyzed Decyanation

Reaction of halogenated pyridines, quinolines, pyrimidines, and pyrazines with potassiophenylacetonitrile (5) in liquid ammonia under near-uv irradiation affords secondary nitriles, which then undergo oxidative decyanation under phase-transfer catalytic conditions to afford aryl hetaryl ketones in excellent yields.

A NEW SYNTHESIS OF SOME NON-STEROIDAL ANTI-INFLAMMATORY AGENTS VIA CYANOPHOSPHATES

A simple and convenient procedure for the syntheses of some non-steroidal anti-inflammatory agents, ibuprofen, rac-naproxen, clidanac and loxoprofen, is described.