1613-94-1

Basic information

• Product Name: Benzenamine, 4-nitro-N-(phenylmethylene)-, (E)-
• CAS NO: 1613-94-1
• Molecular Formula: C13H10N2O2
• Molecular Weight: 226.235
• Mol File: 1613-94-1.mol
• Article Data: 82

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-nitro-N-(phenylmethylene)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-nitro-N-(phenylmethylene)-, (E)-(1613-94-1)
• EPA Substance Registry System: Benzenamine, 4-nitro-N-(phenylmethylene)-, (E)-(1613-94-1)

Safety Data

• Hazardous Substances Data: 1613-94-1(Hazardous Substances Data)

Upstream product

• 538-51-2 benzylidene phenylamine 
• 100-01-6 4-nitro-aniline 
• 92-29-5 hydrobenzamide 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 101025-17-6 [(Z)-4-Nitro-phenylimino]-phenyl-acetic acid 
• 100-52-7 benzaldehyde 
• 53847-22-6 C₂₄H₁₉AsN₂O₂ 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 107866-78-4 N,N'-bis-(4-nitro-phenyl)-benzylidenediamine 
• 1516-60-5 4-nitrophenyl azide 
• 108-88-3 toluene 
• 27845-53-0 (E)-N-cyclohexyl-1-phenylmethanimine 
• 100-46-9 benzylamine 

Downstream Products

• 5502-63-6 p-nitrosuccinanilic acid 
• 807-71-6 β-4-Nitro-anilino-β-phenyl-4-nitro-propiophenon 
• 1187159-26-7 C₁₈H₂₀N₂O₂ 
• 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 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 100-01-6 4-nitro-aniline 
• 138432-74-3 6-nitro-2,4-diphenyl-quinoline 
• 14309-92-3 N-benzyl-4-nitroaniline 
• 107866-78-4 N,N'-bis-(4-nitro-phenyl)-benzylidenediamine 
• 54397-18-1 2-phenyl-3-p-nitrophenyl-1,3-thiazolidin-4-one 

Relevant articles and documents

T3P-promoted synthesis of a series of novel 3-aryl-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

A series of 11 novel 3-aryl-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-aryl-C-phenyl imines with thiosalicylic acid. This provides simple and ready access to N-aryl compounds in this family, which have been generally difficult to prepare.

Reaction of nitroanilines with aldehydes. Refinement of the Doebner–Miller reaction mechanism

Due to intramolecular hydrogen bonding between the amino and nitro groups, o-nitroaniline is incapable of forming Schiff bases in the reactions with acetaldehyde and crotonaldehyde but is converted to quinoline derivative under Doebner–Miller reaction conditions via addition to the C=C double bond of the α,β-unsaturated aldehyde. Under analogous conditions, p-nitroaniline possessing a free amino group gives rise to the product of Doebner–Miller quinoline synthesis through intermediate formation of Schiff base dimer. The reaction of p-nitroaniline with benzaldehyde also yields the corresponding Schiff base, whereas o-nitroaniline is converted to N-benzyl derivative.

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Photochemically Promoted Aza-Diels-Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation

Aza-Diels-Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 °C), affording the cycloaddition product in 97% yield.

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.

Catalytic activity of Mg-Al hydrotalcites and derived mixed oxides for imination reactionsviaan oxidative-dehydrogenation mechanism

The catalytic activities of Mg-Al hydrotalcites and derived Mg-Al mixed oxides were studied for the imination of benzylic substrates (benzyl amine and benzyl alcohol), with aniline as a model reaction, to establish a green and cost-effective catalytic (precious metal free) process for imination and tandem reactions utilizing alcohols as reagents. The Mg-Al mixed oxide (Mg/Al ratio = 3.0) was found to be an efficient catalyst for imination reactions to synthesize cross-imines with high selectivity as well as for tandem reactions of alcohols. Basic sites of catalysts adsorb benzylic substrates through the hydrogen of their functional groups (-NH2/-OH) and activate (weaken) benzylic C-H bonds for hydride elimination. Thus, basic sites catalyze the reaction by activating benzylic substrates for oxidative-dehydrogenation (i.e., deprotonation followed by hydride elimination with the help of oxygen) to produce reactive imine/carbonyl intermediates, which undergo subsequent nucleophilic reactions with amine.