571903-59-8

Basic information

• Product Name: 3-(phenylamino)benzonitrile
• Synonyms: 3-(phenylamino)benzonitrile
• CAS NO: 571903-59-8
• Molecular Formula: C13H10N2
• Molecular Weight: 194.2319
• Mol File: 571903-59-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(phenylamino)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(phenylamino)benzonitrile(571903-59-8)
• EPA Substance Registry System: 3-(phenylamino)benzonitrile(571903-59-8)

Safety Data

• Hazardous Substances Data: 571903-59-8(Hazardous Substances Data)

Upstream product

• 586-96-9 Nitrosobenzene 
• 571903-65-6 (3-cyanophenyl)magnesium chloride 
• 1198183-95-7 phenyl 1H-imidazole-1-sulfonate 
• 2237-30-1 m-cyanoaniline 
• 591-50-4 iodobenzene 
• 62-53-3 aniline 
• 214360-46-0 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 
• 69113-59-3 3-iodobenzonitrile 
• 108-94-1 cyclohexanone 
• 108-95-2 phenol 
• 143-66-8 sodium tetraphenyl borate 

Relevant articles and documents

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.

Copper-Catalyzed NaBAr 4-Based N-Arylation of Amines

Using NaBAr 4 as an arylating agent, the formation of carbon-heteroatom bonds by a Cham-Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr 4 proceeds smoothly to offer the corresponding products in good to excellent yields.

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides

In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.

Highly Chemoselective Iridium Photoredox and Nickel Catalysis for the Cross-Coupling of Primary Aryl Amines with Aryl Halides

A visible-light-promoted iridium photoredox and nickel dual-catalyzed cross-coupling procedure for the formation C?N bonds has been developed. With this method, various aryl amines were chemoselectively cross-coupled with electronically and sterically diverse aryl iodides and bromides to forge the corresponding C?N bonds, which are of high interest to the pharmaceutical industries. Aryl iodides were found to be a more efficient electrophilic coupling partner. The coupling reactions were carried out at room temperature without the rigorous exclusion of molecular oxygen, thus making this newly developed Ir-photoredox/Ni dual-catalyzed procedure very mild and operationally simple.

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device containing the same. The organic electroluminescent compounds according to the present invention have high luminescent efficiency and a lo

Palladium- and nickel-catalyzed aminations of aryl imidazolylsulfonates and sulfamates

A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.

Preparation of polyfunctional amines by the addition of functionalized organomagnesium reagents to nitrosoarenes

The addition of functionalized arylmagnesium reagents to nitrosoarenes at -20°C in THF furnishes after a reductive work-up polyfunctional diarylamines in 43-74% yield.