785-81-9

Basic information

• Product Name: benzylidene-(4-nitrophenyl)amine
• Synonyms: benzylidene-(4-nitrophenyl)amine;N-(4-nitrophenyl)-1-phenylmethanimine;N-(4-nitrophenyl)-1-phenyl-methanimine
• CAS NO: 785-81-9
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.2307
• Mol File: 785-81-9.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 399.6°Cat760mmHg
• Flash Point: 195.5°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 3.12E-06mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: benzylidene-(4-nitrophenyl)amine(CAS DataBase Reference)
• NIST Chemistry Reference: benzylidene-(4-nitrophenyl)amine(785-81-9)
• EPA Substance Registry System: benzylidene-(4-nitrophenyl)amine(785-81-9)

Safety Data

• Hazardous Substances Data: 785-81-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10N2O2/c16-15(17)13-8-6-12(7-9-13)14-10-11-4-2-1-3-5-11/h1-10H/b14-10+

Upstream product

• 100-01-6 4-nitro-aniline 
• 92-29-5 hydrobenzamide 
• 101025-17-6 [(Z)-4-Nitro-phenylimino]-phenyl-acetic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 538-51-2 benzylidene phenylamine 
• 1516-60-5 4-nitrophenyl azide 
• 108-88-3 toluene 
• 100-52-7 benzaldehyde 
• 15484-91-0 N-benzylidene-4-ethoxyaniline 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 7519-65-5 N-(3-chlorobenzylidene)aniline 
• 5341-44-6 N-(3-nitrobenzylidene)aniline 

Downstream Products

• 5502-63-6 p-nitrosuccinanilic acid 
• 7669-49-0 N-(4-nitrophenyl)-N'-phenylthiourea 
• 41226-87-3 2,3-bis-(4-nitro-phenyl)-4-phenyl-oxazolidine-5,5-dicarbonitrile 
• 5729-41-9 N--N'--harnstoff 
• 107866-78-4 N,N'-bis-(4-nitro-phenyl)-benzylidenediamine 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 100-01-6 4-nitro-aniline 
• 74650-16-1 N-(4-nitrophenyl)-2-phenyl-aziridine 
• 19348-89-1 diphenyl {[(4-nitrophenyl)amino](phenyl)methyl}phosphonate 
• 130232-05-2 cis-N-p-nitrophenyl 3-ethoxycarbonyl-2,2-dimethyl-4-phenyl-4-butanelactam 
• 130232-05-2 trans-N-p-nitrophenyl 3-ethoxycarbonyl-2,2-dimethyl-4-phenyl-4-butanelactam 
• 75158-89-3 C₃₃H₂₅N₃O₄S₂ 
• 70869-76-0 3,4-dihydro-7-nitro-3-phenyl-2H-benzothiazine 1,1-dioxide 

Relevant articles and documents

Triarylmethyl Cation-Catalyzed Three-Component Coupling for the Synthesis of Unsymmetrical Bisindolylmethanes

An efficient synthesis of unsymmetrical bisindolylmethanes has been accomplished using triarylmethyl cations to catalyze the reaction of N-arylimines with two different indoles. Optimization of the organocatalyst by tuning cation stability allows for excellent single addition selectivity when coupled with p-nitrophenyl imines. The optimal catalyst is commercially available, and the reaction minimizes waste and environmental impact by employing a one-to-one ratio of starting materials. The intermediates can be isolated or used in situ in a one-pot two-step reaction to generate unsymmetrical bisindolylmethanes in high yields. The reaction tolerates a broad range of imines with the highest yields observed for electron-poor and neutral imines. A wide range of indole nucleophiles are also successfully employed allowing for the creation of a large variety of unsymmetrical bisindolylmethanes.

Cyclometalated Half-Sandwich Iridium(III) Complexes: Synthesis, Structure, and Diverse Catalytic Activity in Imine Synthesis Using Air as the Oxidant

Four air-stable cyclometalated half-sandwich iridium complexes 1-4 with C,N-donor Schiff base ligands were prepared through C-H activation in moderate-to-good yields. These complexes have been well characterized, and their exact structure was elaborated on by single-crystal X-ray analysis. The iridium(III) complexes 1-4 showed good catalytic activity in the imine synthesis under open-flask conditions (air as the oxidant) from primary amine oxidative homocoupling, secondary amine dehydrogenation, and the cross-coupling reaction of amine and alcohol. Substituents bonded on the ligands of the iridium complexes displayed little effect on the catalytic efficiency. The stability and good catalytic efficiency of the iridium catalysts, mild reaction conditions, and substrate universality showed their potential application in industrial production.

Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ

A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.