344400-43-7

Basic information

• Product Name: C₉H₈N₂
• Synonyms: C₉H₈N₂
• CAS NO: 344400-43-7
• Molecular Weight: 144.176
• Mol File: 344400-43-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: C₉H₈N₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₉H₈N₂(344400-43-7)
• EPA Substance Registry System: C₉H₈N₂(344400-43-7)

Safety Data

• Hazardous Substances Data: 344400-43-7(Hazardous Substances Data)

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 107-13-1 acrylonitrile 
• 62-53-3 aniline 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 1379407-67-6 C₁₀H₈N₂O 
• 1448709-55-4 2-(2-(phenylthio)-1H-indol-3-yl)acetonitrile 
• 612-96-4 2-Phenylquinoline 
• 27005-52-3 2-(2-phenyl-1H-indol-3-yl)acetonitrile 

Relevant articles and documents

Synthesis of Highly Substituted 2-Arylindoles via Copper-Catalyzed Coupling of Isocyanides and Arylboronic Acids

Highly functionalized 2-arylindoles were synthesized from 2-alkenylarylisocyanides and arylboronic acids using a simple, inexpensive copper catalyst. The reaction exhibits excellent functional group tolerance for both the arylisocyanide and boronic acid coupling partners. To avoid the direct handling of the pungent arylisocyanide starting materials, continuous flow chemistry is further demonstrated to provide safe and effective access to 2-arylindoles through in situ dehydration and cyclization of easy-to-handle 2-alkenyl-N-formylanilines.

Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process

A radical cascade process initiated through visible-light induced thiyl radical coupling with ortho-substituted arylisocianides followed by an intramolecular cyclization and subsequent aromatization to access 2-sulfenylindoles is described. The key thiyl radicals are promptly generated via a hydrogen atom transfer event. The redox-neutral protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions. Furthermore, the implementation of a continuous flow variant allows smooth scalability with a short residence time through process intensification.

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.