67421-66-3

Usage

Type of compound

Aromatic heterocyclic organic compound 2,5-diphenyl-1H-pyrrole-3-carbonitrile is a pyrrole derivative, which is a type of aromatic heterocyclic organic compound known for its stable and aromatic structure.

Usage in organic synthesis

The compound is used in organic synthesis, which means it can be used as a building block or reactant in the creation of more complex organic molecules.

Pharmacological properties

2,5-diphenyl-1H-pyrrole-3-carbonitrile has been studied for its potential pharmacological properties, including its ability to act as an inhibitor for certain enzymes, which could make it useful in drug development.

Physical state and solubility

Solid crystalline substance The compound is a solid with a crystalline structure, and it is insoluble in water but soluble in organic solvents.

Chemical structure

Pyrrole ring with two phenyl groups and a carbonitrile group The compound's structure consists of a pyrrole ring (a five-membered ring with one nitrogen atom) with two phenyl groups (carbon rings with six atoms) attached to it and a carbonitrile group (a triple-bonded carbon atom connected to a nitrogen atom).

Versatility and potential applications

The compound has potential applications in various fields, including drug development and materials science, due to its unique structure and properties.

Upstream product

• 151-50-8 potassium cyanide 
• 532-27-4 1-chloroacetophenone 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 28168-60-7 2,5-diphenyl-3,4-dihydro-2H-pyrrole-3-carbonitrile 
• 14476-72-3 2-(2-oxo-2-phenylethyl)malononitrile 
• 98-80-6 phenylboronic acid 
• 79892-21-0 2-benzoyl-4-oxo-4-phenylbutanenitrile 
• 61795-22-0 (1-azidoethene-1,2-diyl)dibenzene 
• 952-06-7 deoxybenzoin oxime 
• 451-40-1 phenyl benzyl ketone 
• 1070-71-9 propiolonitrile 
• 67-56-1 methanol 
• 86625-53-8 4-Diazo-2,5-diphenyl-4H-pyrrole-3-carbonitrile 

Downstream Products

• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 205751-50-4 4-Bromo-2,5-diphenyl-1H-pyrrole-3-carbonitrile 
• 86625-51-6 4-Amino-2,5-diphenyl-1H-pyrrole-3-carbonitrile 
• 86625-48-1 4-cyano-2,5-diphenyl-3-nitropyrrole 

Relevant academic research and scientific papers

Cascade Reactions to Substituted 1 H -Pyrrole-3-carbonitriles via Ligand-Free Palladium(II)-Catalyzed C(sp)-C(sp 2) Coupling

An efficient and simple synthesis of substituted 1 H -pyrrole-3-carbonitriles was developed. This reaction is a palladium(II)-catalyzed cascade of C(sp)-C(sp 2) coupling followed by intramolecular C-N bond formation. The method can tolerate various substrates with satisfactory yields. Its ligand-free conditions and high efficiency make this method particularly attractive.

Visible-light-accelerated pd-catalyzed cascade addition/ cyclization of arylboronic acids to γ- And β-ketodinitriles for the construction of 3-cyanopyridines and 3-cyanopyrrole analogues

The one-pot synthetic strategies for 2,4,6-triarylnicotinonitriles and 2,5-diaryl-1H-pyrrole-3-carbonitriles have been accomplished via a Pd-catalyzed coupling of arylboronic acid with 2-(3-oxo-1,3-diarylpropyl)malononitrile and 2-(2-oxo-2- arylethyl)malo

One-Pot Synthesis of 2-Cyano-1,4-diketones: Applications to Synthesis of Cyanosubstituted Furans, Pyrroles, and Dihydropyridazines

A convenient synthetic route for the construction of functionalized 2-cyano-1,4-diketones has been established from the nucleophilic substitution of 2-bromoacetophenones with NaCN via the in situ-generated β-ketonitriles. This method was further applied to the synthesis of cyanosubstituted furans, pyrroles, or dihydropyridazines, which were obtained in good to excellent yields using Bi(OTf)3, NH4OAc, or N2H4. The key structures were confirmed by X-ray single crystal diffraction analysis.

[3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes

A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.

Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.

The photochemistry of 2-diazo- and 3-diazopyrroles

The photochemistry of 2-diazo- and 3-diazopyrroles has been investigated. The irradiation of 2-diazo-3-cyano-4-methyl-5-phenylpyrrole in various reaction solvents brings to a photolytic singlet carbene intermediate, which evolves into 2-substituted pyrroles. A substituent effects has been recognized in the irradiations of some 3-diazopyrroles in methanol.