785-80-8

Basic information

• Product Name: (p-Nitrobenzylidene)aniline
• Synonyms: (p-Nitrobenzylidene)aniline;N-(p-Nitrobenzylidene)aniline;N-Phenyl(4-nitrophenyl)methaneimine;N-Phenyl-4-nitrobenzylideneamine;p-Nitrobenzaldehyde anil
• CAS NO: 785-80-8
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 0
• Mol File: 785-80-8.mol

Chemical Properties

• Boiling Point: 382.642°C at 760 mmHg
• Flash Point: 185.216°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: (p-Nitrobenzylidene)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: (p-Nitrobenzylidene)aniline(785-80-8)
• EPA Substance Registry System: (p-Nitrobenzylidene)aniline(785-80-8)

Safety Data

• Hazardous Substances Data: 785-80-8(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Synthesis:
(p-Nitrobenzylidene)aniline is used as a colorant in the dye and pigment industry due to its strong absorption of light in the visible region, contributing to the vibrant colors in various applications.
Used in Organic Synthesis:
In the field of organic synthesis, (p-Nitrobenzylidene)aniline serves as a reagent, particularly in the preparation of pharmaceuticals and fine chemicals, where its unique chemical properties are harnessed to facilitate the synthesis of complex molecules.
Used in Medical Research:
(p-Nitrobenzylidene)aniline has been studied for its antibacterial properties and is explored for potential applications in medical research, aiming to develop new treatments or enhance existing ones.
Caution:
It is crucial to handle (p-Nitrobenzylidene)aniline with care, as it is toxic if ingested or inhaled and can cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken to minimize exposure and ensure the well-being of those working with (p-Nitrobenzylidene)aniline.

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

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 62-53-3 aniline 
• 10359-18-9 N-(4-nitrobenzyl)aniline 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 3585-90-8 N-(4-nitrobenzylidene)aniline N-oxide 
• 619-73-8 4-nitrobenzyl chloride 
• 10480-05-4 N-(4-nitrobenzylidene)-4-nitroaniline 
• 1312150-32-5 dimethyl 2-(4-nitrobenzylidene)-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate 
• 135-19-3 β-naphthol 
• 117649-25-9 2-(4-nitro-benzylidenamino)-phenol 
• 7409-30-5 p-nitrobenzylamine 
• 99-99-0 1-methyl-4-nitrobenzene 
• 1227476-15-4 Azobenzene 
• 64-10-8 phenyl carbamate 

Downstream Products

• 14563-27-0 2-(4-nitro-phenyl)-3,6-diphenyl-2,3-dihydro-[1,3,5]thiadiazin-4-one 
• 40046-83-1 2-(4-nitro-phenyl)-3-phenyl-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 58120-00-6 N,N'-Bis-(4-nitrobenzyliden)-sulfamid 
• 68271-44-3 N-[Chloro-(4-nitro-phenyl)-methyl]-2-(3,4-dimethoxy-phenyl)-N-phenyl-acetamide 
• 874-90-8 4-methoxybenzonitrile 
• 39082-45-6 β,β-Bis-(phenylsulfonyl)-4-nitrostyrol 
• 3460-11-5 4-nitrobenzanilide 

Relevant articles and documents

A DFT and experimental study of the spectroscopic and hydrolytic degradation behaviour of some benzylideneanilines

The spectroscopic and hydrolytic degradation behaviour of some N-benzylideneanilines are investigated experimentally and theoretically via high quality density function theoretical (DFT) modelling techniques. Their absorption and vibrational spectra, accurately predicted by DFT calculations, are highly dependent on the nature of the substituents on the aromatic rings, hence, though some of their spectroscopic features are similar, energetic differences exist due to differences in their electronic structures. Whereas the o-hydroxy aniline derived adducts undergo hydrolysis via two pathways, the most energetically economical of which is initiated by a fast enthalpy driven hydration, over a conservative free energy (ΔG?) barrier of 53 kJ mol?1, prior to the rate limiting entropy controlled lysis step which occurs via a conservative barrier of ca.132 kJ mol?1, all other compounds hydrolyse via a slower two-step pathway, limited by the hydration step. Barriers heights for both pathways are controlled primarily by the structure and hence, stability of the transition states, all of which are cyclic for both pathways.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Efficient imine synthesisviaoxidative coupling of alcohols with amines in an air atmosphere using a mesoporous manganese-zirconium solid solution catalyst

Direct oxidative coupling of alcohols with amines using a non-precious metal oxide catalyst under mild conditions is highly desirable for imine synthesis. In this work, a mesoporous Mn1ZrxOysolid solution catalyst prepared by a co-precipitation method showed excellent catalytic performance in imine synthesis from primary alcohols and amines without base additives in an air atmosphere. XRD, N2physisorption, H2-TPR, O2-TPD, EPR and XPS were comprehensively used to unravel its structural, redox and amphoteric properties that closely depended on the interaction between MnOyand ZrO2with a variable Zr ratio. The Mn1Zr0.5Oycatalyst presented the highest fractions of Mn3+ions and reactive oxygen species on the surface, and the highest concentrations of acidic-basic sites, which were disclosed to play important roles in activating alcohols and molecular O2in the rate-determining step. In the model reaction of oxidative coupling of benzyl alcohol with aniline, such enhanced features of the Mn1Zr0.5Oycatalyst can promote the intrinsic catalytic activity (iTOF of 1.87 h?1) and boost benzylideneaniline formation (5.56 mmol gcat.?1h?1) based on a >99% yield at 80 °C respectively at a fast response. It can also work effectively at a room temperature of 30 °C, as well as for the gram-grade synthesis. This is one of the best results among all the MnOy-based catalysts in the literature. Moreover, this catalyst showed good stability and a wide substrate scope with good to excellent yields of imines.

Nanomagnetic catalysis (Fe3O4@S–TiO2): a novel magnetically nano catalyst for the synthesis of new highly substituted tetrahydropyridine derivatives under solvent-free conditions

A novel nanomagnetic catalyst (Fe3O4@S–TiO2) was prepared by the hydrothermal method. At the first, Fe3O4 nanoparticles were synthesized, then iron oxide nanoparticles (IONPs) were dispersed in ethano

Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams

We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.

Borrowing hydrogen activity of NH2-MIL-125 for N-alkylation of amines with alcohols under solvent and base free condition

The NH2-MIL-125 showed excellent activity in solvent and base free N-alkylation of amines with alcohols via borrowing hydrogen mechanism. The Ti–O clusters of NH2-MIL-125 provide acidic-basic active sites for the catalysis of reaction. The NH2-MIL-125 was found to be stable and reusable in the reaction.

Simple synthesis of the novel Cu-MOF catalysts for the selective alcohol oxidation and the oxidative cross-coupling of amines and alcohols

A novel porous metal–organic framework {Cu2(bbda)0.5(Hbbda)1.5(OAc)1.5.8H2O} (UoB-5) was synthesized under ultrasound irradiation by employing a new Schiff base ligand H2bbda (4,4'(1,4-phenylene bis (azanylylidene)) bis (methanylylidene))dibenzoic acid) and was fully characterized. The microporous nature of UoB-5 was confirmed by gas-sorption measurements. This framework acted as a highly effective heterogeneous catalyst for the alcohol oxidation reaction with tert-butyl hydroperoxide (t-BuOOH) as an oxidant. The presence of coordinatively unsaturated metal sites in UoB-5 could be the reason for high performance in this reaction. Furthermore, using the long linker with the free -NC group and uncoordinated -N atom on the wall of the pores created UoB-5 an excellent candidate for the catalytic activities without activation of the framework. It was confirmed with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from benzyl alcohols and anilines. Eventually, the new Cu-MOF (UoB-5) could be an alternative catalyst as a more economically favorable and environmentally friendly in the catalysis field.

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.

Ultrasound-assisted construction of a Z-scheme heterojunction with g-C3N4 nanosheets and flower-like Bi2WO6 microspheres and the photocatalytic activity in the coupling reaction between alcohols and amines under visible light irradiation

Flower-like Bi2WO6 microspheres and bulk g-C3N4 were prepared by the hydrothermal method and high-temperature calcining method, respectively. A new method based on the combination of ultrasonic stripping and mechanical stirring was used to obtain uniform composite x-Bi2WO6/g-C3N4 (x is the Bi2WO6 mass ratio) photocatalysts with a Z-scheme heterojunction. In the reaction of benzyl alcohol and aniline to form imine, the optimal composite, 30percent-Bi2WO6/g-C3N4, showed a conversion rate of 87.6percent, which is much higher than that of pure Bi2WO6 and g-C3N4. Characterization by SEM and TEM showed that the ultrasonically stripped g-C3N4 significantly reduced the radial dimension compared to bulk g-C3N4. A uniformly dispersed photocatalytic material was formed, and it maintained a flower-like microsphere structure. Materials characterized by N2 adsorption–desorption isotherms (BET) showed that the specific surface area of the g-C3N4 nanosheets increased by approximately ten times after ultrasonic stripping. The photostability of the composite was verified by cyclic experiments. Under visible light irradiation, the activation energy of the coupling reaction between benzyl alcohol and aniline was found to be decreased by 29.8 kJ mol?1. A capture experiment was used to verify the active species in the photocatalytic system, with the reaction found to be mainly completed through the synergistic action of h+, e? and ?O2?.