14309-92-3

Basic information

• Product Name: N-benzyl-4-nitroaniline
• Synonyms: N-(4-Nitrophenyl)benzenemethanamine;N-(4-Nitrophenyl)benzylamine;Benzenemethanamine, N-(4-nitrophenyl)-;Einecs 238-249-4;p-Nitro-N-benzylaniline;N-Benzyl-N-(4-nitrophenyl)amine
• CAS NO: 14309-92-3
• Molecular Formula: C₁₃H₁₂N₂O₂
• Molecular Weight: 228.25
• EINECS: 238-249-4
• Mol File: 14309-92-3.mol
• Article Data: 129

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 392 °C at 760 mmHg
• Flash Point: 190.9 °C
• Appearance: /
• Density: 1.258 g/cm³
• Vapor Pressure: 2.36E-06mmHg at 25°C
• Refractive Index: 1.658
• PKA: 0.31±0.20(Predicted)
• CAS DataBase Reference: N-benzyl-4-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-4-nitroaniline(14309-92-3)
• EPA Substance Registry System: N-benzyl-4-nitroaniline(14309-92-3)

Safety Data

• Hazardous Substances Data: 14309-92-3(Hazardous Substances Data)

Usage

General Description

N-Benzyl-4-nitroaniline is a compound bearing both amine and nitro functional groups attached to different locations. It can be distinguished by its yellow appearance and can easily be mass-produced in a laboratory setting. The chemical formula for N-benzyl-4-nitroaniline is C13H12N2O2. Due to the presence of its nitro group, this compound is quite reactive, especially under reduction conditions, making it useful in the production of various dyes, pharmaceuticals, and rubber chemicals. Like many chemicals with similar properties, it needs to be handled with care to avoid eye and skin contact and inhaling as it may be harmful or cause irritation.

InChI:InChI=1/C13H12N2O2/c16-15(17)13-8-6-12(7-9-13)14-10-11-4-2-1-3-5-11/h1-9,14H,10H2

Upstream product

• 85046-51-1 N-nitroso N-benzyl-N-(4-nitroaniline) 
• 100-44-7 benzyl chloride 
• 100-01-6 4-nitro-aniline 
• 56-23-5 tetrachloromethane 
• 100-16-3 4-nitrophenylhydrazone 
• 100-00-5 4-chlorobenzonitrile 
• 100-46-9 benzylamine 
• 350-46-9 4-Fluoronitrobenzene 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 1613-94-1 (E)-N-benzylidene-4-nitroaniline 
• 100-39-0 benzyl bromide 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 100-52-7 benzaldehyde 
• 98-95-3 nitrobenzene 

Downstream Products

• 17272-83-2 N¹-benzyl-benzene-1,4-diamine 
• 104226-37-1 N-benzyl-N-methyl-4-nitroaniline 
• 104226-31-5 N-benzyl-N-methyl-p-phenylenediamine 
• 110137-65-0 N-<4-<(phenylamethyl)amino>phenyl>acetamide 
• 138432-74-3 6-nitro-2,4-diphenyl-quinoline 
• 106-50-3 1,4-phenylenediamine 
• 36934-14-2 O,O'-diethyl [(4-nitrophenylamino)(phenyl)methyl]phosphonate 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 

Relevant articles and documents

Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis

Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.

Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols

A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Rate and Yield Enhancements in Nucleophilic Aromatic Substitution Reactions via Mechanochemistry

A variety of nucleophilic aromatic substitution reactions were carried out mechanochemically to great advantage. On average, reactions rates were nine-times faster. The corresponding kinetic studies presented provide the clearest head-to-head kinetic comparisons between mechanochemical and conventional systems at identical temperatures. Attempts are provided at classifying the kinetics of one example. Removal of polar, protic solvents from these reactions presents environmental benefits to a reaction class whose kinetics are heavily dependent on such solvents.