18613-55-3

Basic information

• Product Name: N,N-Dibenzyl-p-anisidine
• Synonyms: N,N-Dibenzyl-4-methoxyaniline;n,n-dibenzyl-p-anisidine;N-(4-Methoxyphenyl)-N-(phenylmethyl)benzenemethanamine;N-Benzyl-N-(4-methoxyphenyl)benzenemethanamine;Einecs 242-447-6
• CAS NO: 18613-55-3
• Molecular Formula: C₂₁H₂₁NO
• Molecular Weight: 303.4
• EINECS: 242-447-6
• Mol File: 18613-55-3.mol

Chemical Properties

• Boiling Point: 470.2 °C at 760 mmHg
• Flash Point: 136.8 °C
• Appearance: /
• Density: 1.112 g/cm³
• Vapor Pressure: 5.17E-09mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: N,N-Dibenzyl-p-anisidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dibenzyl-p-anisidine(18613-55-3)
• EPA Substance Registry System: N,N-Dibenzyl-p-anisidine(18613-55-3)

Safety Data

• Hazard Codes: N
• Statements: 22-50/53
• Hazardous Substances Data: 18613-55-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dibenzyl-p-anisidine is used as a key intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines. Its ability to form complex organic molecules makes it an essential component in the production of various medications.
Used in Dye Industry:
In the dye industry, N,N-Dibenzyl-p-anisidine is utilized as an intermediate for the production of dyes. Its chemical properties allow for the creation of a range of colorants used in various applications, including textiles, plastics, and printing inks.
Used in Catalyst Industry:
N,N-Dibenzyl-p-anisidine is used as a precursor in the synthesis of catalysts, which are vital in accelerating chemical reactions across numerous industrial processes. Its role in creating catalysts enhances the efficiency and effectiveness of these reactions.
Used in Rubber Industry:
As a reagent in the production of rubber accelerators, N,N-Dibenzyl-p-anisidine is used to speed up the vulcanization process in rubber manufacturing. This application is crucial for improving the production efficiency and the quality of rubber products.

InChI:InChI=1/C21H21NO/c1-23-21-14-12-20(13-15-21)22(16-18-8-4-2-5-9-18)17-19-10-6-3-7-11-19/h2-15H,16-17H2,1H3

Upstream product

• 100-44-7 benzyl chloride 
• 104-94-9 4-methoxy-aniline 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 100-52-7 benzaldehyde 
• 42080-75-1 tris(4-methoxiphenyloxy)borane 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 100-39-0 benzyl bromide 
• 50-00-0 formaldehyd 
• 98-80-6 phenylboronic acid 
• 100-51-6 benzyl alcohol 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 14774-77-7 p-methoxyphenyllithium 
• 87100-28-5 pinacol benzylboronate 
• 944064-51-1 [2-(hydroxymethyl)phenyl]dimethyl(4-methoxyphenyl)silane 

Downstream Products

• 7472-54-0 N-(p-methoxyphenyl)benzamide 
• 1227403-29-3 2-allyl-N,N-dibenzyl-4-methoxybenzenamine 

Relevant articles and documents

Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents

The development and validation of copper-catalyzed, electrophilic amination of aryl and heteroaryl organolithiums with N,N-dialkyl-O-benzoylhydroxylamines have been achieved exploiting recoverable siloxane transfer agents. Given the ready availability of organolithium compounds, the mild reaction conditions, the ease of product purification, and the ready recovery of the siloxane transfer agents, this transformation comprises a useful tactic to access diverse aryl and heteroaryl amines.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

N-Benzylation of primary amines using magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine as an efficient and recyclable heterogeneous catalyst

Herein we report, a new, simple and mild procedure for N-benzylation and N,N-dibenzylation of anilines through the reaction of aniline derivatives and benzyl bromide at 60 °C in EtOH in the presence of catalytic amounts of magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine (Fe3O4?SiO2?Propyl-HMTA). The title compounds were formed in high purity and their structures characterized by spectral analysis. The results also showed that the magnetic nanoparticle catalyst had significant advantages including, simplicity of preparation, heterogeneity, stability and recyclability. Moreover, the catalyst was characterized by various methods, such as FT-IR, SEM, VSM, TEM, TGA and XRD, after the reaction to compare with its structure before reaction.

Ruthenium nanoparticle catalyzed selective reductive amination of imine with aldehyde to access tertiary amines

Reductive amination is one of the most frequently used transformations in organic synthesis. Herein, we developed a novel ruthenium nanoparticle embedded ordered mesoporous carbon catalyst (Ru-OMC) and a new hydrosilylation process for the synthesis of tertiary amines. We present a direct reductive amination of imines (CN bond) with aldehydes (CO bond) using hydrosilane as the reducing reagent under mild conditions. Moreover, the Ru-OMC catalysts can be reused for up to 14 runs without noticeably losing activity.

MIL-101(Cr) as a synergistic catalyst for the reduction of imines with trichlorosilane

The development of catalyst based on porous crystalline materials (PCM) constructed from metal ions or clusters and multidentate organic ligands is a topic of great interest. In view of the Lewis acidic and basic properties of PCMs, we report for the first time that MIL-101(Cr) works as a synergistic catalyst for the reduction of imines with trichlorosilane as the hydrogen source. Both ketimines and aldimines were tolerated with this protocol, giving the corresponding amines in moderate to high yields. The operational simplicity as well as mild reaction conditions renders this protocol an attractive approach for the synthesis of amines. Furthermore, a chiral MOF, CMIL-101, was also realized by grafting chiral N-formyl proline derivatives to the open metal sites. Moreover, CMIL-101 exhibited a comparable catalytic performance with its homogeneous counterpart in terms of yields and enantioselectivities.

“One pot” synthesis of tertiary amines: Ru(II) catalyzed direct reductive N-benzylation of imines with benzyl bromide derivatives

The direct reductive N-benzylation of imines by reaction with benzyl bromide derivatives, in the presence of [RuCl2(p-cymene)]2catalyst and PhSiH3, is performed under mild conditions without additional base. This reaction proceeds by a tandem imine hydrosilylation/nucleophilic substitution with benzyl bromide derivatives to result the tertiary amines.

Copper-catalyzed electrophilic amination using: N -methoxyamines

Copper-catalyzed electrophilic amination of a triarylboroxin using an N-methoxyamine to give quick access to a variety of anilines was reported. The reaction was especially useful for syntheses of functionalized anilines when combined with our previously reported nucleophilic addition to N-methoxyamides.

SILICON-BASED CROSS COUPLING AGENTS AND METHODS OF THEIR USE

Compositions and methods using silicon-based cross-coupling agents in the formation of carbon-carbon and carbon-nitrogen bonds are described.

A process for preparing amine compound using carbon-supported cobalt-rhodium nanoparticel catalyzed hydrogen-free recuctive amination

The present invention relates to hydrogen-free reductive amination of an aldehyde and/or ketone and an amine and/or nitroarene using cobalt-rhodium heterometal nanoparticles supported on carbon as a non-homogeneous catalyst. According to the present invention, it is possible to carry out amination under significantly lower pressure as compared to the reductive amination carried out in the presence of a conventional rhodium or ruthenium catalyst. In addition, there is no need for using an additional ligand, acid or base. Further, it is possible to use water generated in a reaction system by a water-gas shift reaction as a hydrogen source with no use of an external hydrogen source, and thus to use a solvent without purification. Thus, it is possible to simplify the reaction procedure. The catalyst system according to the present invention provides a simple method for preparing secondary and tertiary amines from various aldehydes and amines.

Iron-catalyzed amination of alcohols assisted by Lewis acid

An efficient Lewis acid-assisted, iron-catalyzed amination of alcohols using borrowing hydrogen methodology was developed. In particular, silver fluoride was identified to be a highly effective additive to overcome the low efficiency in the amination of secondary alcohols catalyzed by Kn?lker's complex.