27005-52-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylindole-3-acetonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its anti-inflammatory and anti-fungal properties. It aids in the development of new drugs by providing a structural foundation that can be further modified to enhance therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Phenylindole-3-acetonitrile serves as a building block in the creation of compounds with anti-fungal properties, contributing to the development of effective crop protection agents.
Used in Organic Synthesis:
2-Phenylindole-3-acetonitrile is utilized as a versatile building block in organic synthesis for the preparation of heterocyclic compounds. Its unique structure allows for the exploration of new chemical pathways and the creation of innovative molecules with potential applications in various fields.
Used in Drug Development:
2-PHENYLINDOLE-3-ACETONITRILE has shown promising results in the development of new drugs, particularly due to its potential applications in medicine. Its presence in the synthesis process can lead to the discovery of novel therapeutic agents with improved efficacy and reduced side effects.

InChI:InChI=1/C16H12N2/c17-11-10-14-13-8-4-5-9-15(13)18-16(14)12-6-2-1-3-7-12/h1-9,18H,10H2

Upstream product

• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 99893-13-7 1-acetyl-1,2-dihydro-2-phenyl-3H-indol-3-one 
• 771-51-7 indole-3-acetonitrile 
• 344400-43-7 C₉H₈N₂ 
• 100-52-7 benzaldehyde 
• 948-65-2 2-phenyl-indole 
• 590-17-0 cyanomethyl bromide 
• 106050-92-4 (2-bromo-1H-indol-3-yl)-acetonitrile 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 1234713-30-4 C₁₆H₁₉BN₂O₂ 
• 36779-17-6 methyl 2-phenyl-1H-indole-3-carboxylate 
• 59050-38-3 2-phenyl-indole-3-carboxylic acid 
• 107734-06-5 N-tosyl-2-phenylindole 

Downstream Products

• 78578-71-9 methyl 1-methyl-2-phenyl-3-indolylcyanoacetate 
• 97945-27-2 2-(2-phenyl-1H-indol-3-yl)acetaldehyde 
• 54885-00-6 phenyl(quinolin-4-yl)methanone 
• 1278540-60-5 C₃₀H₂₂ClNO₃ 
• 1278540-65-0 C₂₃H₁₉NO₂ 
• 1278540-55-8 C₂₃H₁₆ClNO₃ 
• 4662-03-7 2-phenylindole-3-acetic acid 
• 1370733-39-3 N-methyl-2-(2-phenyl-1H-indol-3-yl)ethanamine 
• 1428443-86-0 2-(methyl(2-(2-phenyl-1H-indol-3-yl)ethyl)amino)-1-morpholinoethan-1-one 
• 1217-80-7 2-(2-phenyl-1H-indol-3-yl)ethylamine 

Relevant academic research and scientific papers

Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism

The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.

N-Heterocyclic carbene (NHC)-catalysed atom economical construction of 2,3-disubstituted indoles

A novel organocatalytic approach, harnessing the unique reactivities of N-heterocyclic carbenes (NHCs), has been revealed for the construction of indoles. The NHC-catalysed atom economical synthesis of a wide range of 2-substituted indole-3-acetic acid derivatives is displayed. Strategic application of the developed method was demonstrated for a short synthesis of a cyclin-dependent kinase (CDK) inhibitor: paullone.

New MKLP-2 inhibitors in the paprotrain series: Design, synthesis and biological evaluations

Members of the kinesin superfamily are involved in key functions during intracellular transport and cell division. Their involvement in cell division makes certain kinesins potential targets for drug development in cancer chemotherapy. The two most advanc

Design and synthesis of indomethacin analogues that inhibit P-glycoprotein and/or multidrug resistant protein without Cox inhibitory activity

We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.

Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides

(Figure Presented) We have developed a method for the synthesis of 2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the Suzuki-Miyaura reaction. The utility of this method is demonstrated in the rapid synthesis of a kinase inhibitor, paullone. The reaction can be extended to the synthesis of 2-hydride indole and 2-silylindole by using hydroboronate (or hydrosilane) and silylboronate, respectively. Under these copper-catalyzed conditions, a quinoxaline ring system can also be constructed by using 1,2-isocyanobenzene as a substrate.

Reactions of substituted 2,3-dihydro-1H-indol-3-ones and pyrrolo[2,3-b]pyridin-3-ones with Wittig and Horner-Emmons reagents: Synthesis of 7-azatryptamine

The reactivity of indolinone 1 towards Wittig and Horner-Emmons reactions was reported; the influence of the nature of substituent on the nitrogen atom was examined. 7-Azaindolinone 2 reacted with diethyl cyanomethanephosphonate for giving the corresponding (7-azaindol-3-yl)acetonitrile or more unexpectedly, a C-2 alkylated product; this behavior has been extended to another nucleophilic reagent. Finally the synthesis of 7-azatryptamine was reported.