39065-51-5

Basic information

• Product Name: 4-phenylnicotinonitrile
• Synonyms: 4-phenylnicotinonitrile
• CAS NO: 39065-51-5
• Molecular Formula: C₁₂H₈N₂
• Molecular Weight: 180.209
• Mol File: 39065-51-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-phenylnicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylnicotinonitrile(39065-51-5)
• EPA Substance Registry System: 4-phenylnicotinonitrile(39065-51-5)

Safety Data

• Hazardous Substances Data: 39065-51-5(Hazardous Substances Data)

Usage

General Description

4-phenylnicotinonitrile is a chemical compound with the molecular formula C13H9N3. It is a derivative of nicotinonitrile, with a phenyl group attached to the fourth carbon of the pyridine ring. 4-phenylnicotinonitrile is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable intermediate in organic synthesis, particularly for the production of bioactive compounds and fine chemicals. 4-phenylnicotinonitrile is also known for its potential use as a ligand in coordination chemistry, where it can form stable complexes with metal ions. Overall, this compound has diverse applications in the fields of medicine, agriculture, and materials science.

Upstream product

• 591-50-4 iodobenzene 
• 138823-78-6 3-Cyano-1-ethoxycarbonyl-pyridinium; chloride 
• 100-54-9 pyridine-3-carbonitrile 
• 143806-91-1 3-cyano-1,4-dihydro-1-(dimethylthexylsilyloxy)methyl-4-phenylpyridine 
• 144028-48-8 3-cyano-1-(dimethylthexylsilyloxy)methylpyridinium chloride 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 5061-91-6 9H-indeno(2,1-c)pyridin-9-one 

Relevant articles and documents

Lewis acid-catalyzed borono-minisci reactions of arylboronic acids and heterocycles

A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Br?nsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.

SYNTHESES OF 2-AZAFLUORENONES FROM 3-SUBSTITUTED 4-ARYLPYRIDINES

3-substituted 4-arylpyridines (5a-i) were synthesized in good yields by reaction of mixed copper, zinc aryl organometallics (2a-e) with 1-ethoxycarbonylpyridinium chlorides (1a-d) followed by o-chloranil oxidation under reflux in toluene.The arylpyridines (5a-i) are obtained predominantly.Having compounds (5a-i) in hand, a convenient method was developed for the synthesis of 2-azafluorenones (7a-f) by using cyclization of 4-arylpyridines (5a-i) with phosphoric acid.

Regioselective Addition ofd Copper-Zinc Aryl Organometallic Reagents to 3-substituted Pyridinium Salts

A number of 3-substituted pyridinium salts are subjected to nucleophilic addition by copper-zinc aryl organometallic reagents.The adducts are oxidized subsequently to form the corresponding 4-arylpyridines.In all the cases 1,4-addition products are obtained predominantly.The regioselectivity can be rationalized according to the hard-soft acid-base principle.Calculations on both charge distributions and FMO coefficients indicate that these reactions may be classified on the basis of the type of soft acid-soft base reactions.The observed γ-attack complies very well with the orientation of the FMO coefficients as estimated by a semiempirical method.