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

• 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 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 27845-53-0 (E)-N-cyclohexyl-1-phenylmethanimine 
• 17763-80-3 para-nitrophenyl triflate 
• 7647-01-0 hydrogenchloride 
• 85046-51-1 N-nitroso N-benzyl-N-(4-nitroaniline) 
• 100-51-6 benzyl alcohol 

Downstream Products

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

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.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC

The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.

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.