56511-50-3

Basic information

• Product Name: N,N-dibenzyl-3-methoxyaniline
• CAS NO: 56511-50-3
• Molecular Formula: C₂₁H₂₁NO
• Molecular Weight: 303.3975
• Mol File: 56511-50-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 458.6°C at 760 mmHg
• Flash Point: 133.7°C
• Density: 1.112g/cm³
• Vapor Pressure: 1.36E-08mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: N,N-dibenzyl-3-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dibenzyl-3-methoxyaniline(56511-50-3)
• EPA Substance Registry System: N,N-dibenzyl-3-methoxyaniline(56511-50-3)

Safety Data

• Hazardous Substances Data: 56511-50-3(Hazardous Substances Data)

Upstream product

• 578-57-4 2-bromoanisole 
• 100-39-0 benzyl bromide 
• 536-90-3 m-Anisidine 
• 2398-37-0 3-methoxyphenyl bromide 
• 103-49-1 dibenzylamine 
• 5464-77-7 N,N-dibenzylformamide 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 456-49-5 1-fluoro-3-methoxybenzene 

Downstream Products

• 851085-92-2 (S)-3-(4-Amino-2-methoxy-phenyl)-butan-1-ol 
• 217301-15-0 (3S)-3-(2-Methoxy-4-methylphenyl)butan-2-ol 
• 323195-86-4 (3S)-3-(2-Methoxy-4-methylphenyl)butyl iodide 
• 217301-18-3 (S)-(+)-Curcuphenol methyl ether 
• 1355025-58-9 N,N-dibenzyl-3-methoxy-4-((triisopropylsilyl)ethynyl)aniline 
• 851085-91-1 (S)-3-(4-dibenzylamino-2-methoxy-phenyl)butyraldehyde 

Relevant articles and documents

ARYLATION OF ALIPHATIC AMINES

The invention relates to a method for arylation of amines, such as aliphatic amines by reaction of aryl-halogens, e.g. chloro- or fluorobenzene derivatives without strongly electron withdrawing substituents in the presence of a strong base.

Selective catalytic Hofmann: N -alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides

Using only catalytic amounts of alkyl halides in the reactions of poor nucleophilic amines/amides and alcohols led to a selective Hofmann N-alkylation reaction catalytic in alkyl halides, providing a practical and efficient method for the practical synthesis of mono- or di-alkylated amines/amides in high selectivities. This new method avoids the use of large amounts of bases, alkyl halides, and solvents, and generates water as the only byproduct. Preliminary mechanistic studies showed that alkyl halides are key intermediates/catalysts regeneratable in the reaction cycle.

SiO2-Cu2O: An efficient and recyclable heterogeneous catalyst for N-benzylation of primary and secondary amines

A mild, effective, and selective procedure is reported for the mono N-benzylation and N,N-dibenzylation of primary amines as well as mono N-benzylation of secondary amines using silica-supported copper(I) oxide in water. The silica-supported Cu2O was generated in situ by the reaction of Fehling solution and glucose at 100 C onto activated silica. The catalyst was filtered, washed with water, and oven-dried, and was characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, transmission electron microscopy, and atomic absorption spectroscopy. The prepared Cu2O-SiO2 was found to be thermally stable up to 325 C. The copper was uniformly distributed onto the surface of the silica, and the mean particle diameter was 7 nm. The catalyst served as a selective heterogenous catalyst for the N-benzylation of primary and secondary amines. The catalyst is recyclable and was used effectively upto fifth run without a significant loss of catalytic activity. Various reaction solvents including water, acetonitrile, and toluene were screened for N-benzylation of amines, and the success of the aqueous system highlights the low environmental impact of the procedure.