161957-95-5

Basic information

• Product Name: N-(3,4,5-trimethoxybenzyl)aniline
• Synonyms: N-(3,4,5-trimethoxybenzyl)aniline;N-phenyl-N-(3,4,5-trimethoxybenzyl)amine
• CAS NO: 161957-95-5
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.32696
• Mol File: 161957-95-5.mol

Chemical Properties

• Melting Point: 135 °C(Solv: methanol (67-56-1))
• Boiling Point: 402.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.131±0.06 g/cm3(Predicted)
• PKA: 3.78±0.25(Predicted)
• CAS DataBase Reference: N-(3,4,5-trimethoxybenzyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,4,5-trimethoxybenzyl)aniline(161957-95-5)
• EPA Substance Registry System: N-(3,4,5-trimethoxybenzyl)aniline(161957-95-5)

Safety Data

• Hazardous Substances Data: 161957-95-5(Hazardous Substances Data)

Upstream product

• 114468-30-3 N-(3,4,5-trimethoxybenzylidene)aniline 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 62-53-3 aniline 
• 18638-99-8 3,4,5-trimethoxybenzylamine 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 

Downstream Products

• 114468-30-3 N-(3,4,5-trimethoxybenzylidene)aniline 
• 21878-28-4 6-chloro-2-(4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 

Relevant articles and documents

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

Mimicking transition metals in borrowing hydrogen from alcohols

Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to anin situgenerated imine is the hallmark of a transition metal mediated catalyticN-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established. Herein, we demonstrate that a phenalenyl ligand can imitate the role of transition metals in storing and transferring hydrogen molecules leading to borrowing hydrogen mediated alkylation of anilines by alcohols including a wide range of substrate scope. A close inspection of the mechanistic pathway by characterizing several intermediates through various spectroscopic techniques, deuterium labelling experiments, and DFT study concluded that the phenalenyl radical based backbone sequentially adds H+, H˙ and an electron through a dearomatization process which are subsequently used as reducing equivalents to the C-N double bond in a catalytic fashion.

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.

Mild and efficient synthesis of secondary aromatic amines by one-pot stepwise reductive amination of arylaldehydes with nitroarenes promoted by reusable nickel nanoparticles

The one-pot stepwise reductive amination of arylaldehydes with nitroarenes is described, using reusable nickel nanoparticles (Ni-pol) as catalyst and NaBH4 as mild, inexpensive, and safe reducing agent. The proposed catalytic system holds several advantages such as the use of a non-precious and earth-abundant metal, the facile separation of the catalyst from the reaction mixture by centrifugation, excellent stability towards air and moisture, very mild reaction conditions, good recyclability, broad substrate scope with good to excellent yields, and easy scalability (up to 1.0 g). FESEM analyses indicate that the active species are cubic nanocrystals of Ni in the average cross section value of 35 nm with a quite narrow (25–45 nm) and monomodal distribution, which becomes bimodal with the recycling reactions but without agglomeration.

Synthesis of Symmetric and Unsymmetric Secondary Amines from the Ligand-Promoted Ruthenium-Catalyzed Deaminative Coupling Reaction of Primary Amines

The catalytic system generated in situ from the tetranuclear Ru-H complex with a catechol ligand (1/L1) was found to be effective for the direct deaminative coupling of two primary amines to form secondary amines. The catalyst 1/L1 was highly chemoselective for promoting the coupling of two different primary amines to afford unsymmetric secondary amines. The analogous coupling of aniline with primary amines formed aryl-substituted secondary amines. The treatment of aniline-d7 with 4-methoxybenzylamine led to the coupling product with significant deuterium incorporation on CH2 (18% D). The most pronounced carbon isotope effect was observed on the α-carbon of the product isolated from the coupling reaction of 4-methoxybenzylamine (C(1) = 1.015(2)). A Hammett plot was constructed from measuring the rates of the coupling reaction of 4-methoxyaniline with a series of para-substituted benzylamines 4-X-C6H4CH2NH2 (X = OMe, Me, H, F, CF3) (ρ = -0.79 ± 0.1). A plausible mechanistic scheme has been proposed for the coupling reaction on the basis of these results. The catalytic coupling method provides an operationally simple and chemoselective synthesis of secondary amine products without using any reactive reagents or forming wasteful byproducts.

One-pot stepwise reductive amination reaction by N-coordinate sulfonamido-functionalized Ru(II) complexes in water

New complexes of formula [RuCl(p-cymene)(L)] (7–12) were prepared with [RuCl2(p-cymene)]2 and pre-synthesized N-arenesulfonly-o-phenylenediamines (1–6) and characterized using 1H NMR, 13C NMR, Fourier transform

An Efficient Metal-Free Mono N-Alkylation of Anilines via Reductive Amination Using Hydrosilanes

2-Aminoquinazolin-4-one based efficient organocatalytic eco-friendly reductive amination approach was developed for the mono N-alkylation of anilines using hydrosilane as a reducing agent. This practically easy and sustainable approach works under neat reaction conditions and utilizes non-toxic environmentally benign acetic acid as a dehydrating agent. The developed protocol have several advantages, such as broad substrate scope, wide functional group tolerance, short reaction time, and absence of metal catalyst in the reaction.

Implications of dynamic imine chemistry for the sustainable synthesis of nitrogen heterocycles via transimination followed by intramolecular cyclisation

An exploration of a tandem approach to the sustainable synthesis of N-heterocycles from readily available N-aryl benzylamines or imines and ortho-substituted anilines is described, which demonstrates, for the first time, an important synthetic application of dynamic imine chemistry. The key features to the successful development of this protocol include the utilisation of N-aryl benzylamines as imine precursors in transimination, the occurrence of transimination in acetonitrile in the absence of any catalysts, an intramolecular nucleophilic addition occurring in the newly formed imine causing irreversible transimination, and the tandem event occurring under green conditions.

Aerobic oxidation of amines catalyzed by polymer-incarcerated au nanoclusters: Effect of cluster size and cooperative functional groups in the polymer

Aerobic oxidation reaction of amines to imines catalyzed by polymer-incarcerated Au nanoclusters (PI-Au) was developed. The effect of cluster size for this oxidation reaction was carefully examined using the same polymer support. We have succeeded in preparation of various PI-Au catalysts containing different size clusters by modification of standard preparation methods. The size of clusters and their distribution were analyzed by electron microscopy. Interestingly, catalysts containing relatively larger clusters (>5 nm) showed higher activity in aerobic oxidation of amines than catalysts containing smaller clusters (13 nm) that showed much better activity for aerobic oxidation of alcohols. In addition, novel Au nanocluster catalysts immobilized on newly prepared polymer with tertiary amine groups were developed and they showed excellent activity for aerobic oxidation of amines to imines. The relation between cluster size and catalytic activity and role of tertiary amine in polymer were discussed. These catalysts could be applied to aerobic oxidative deprotection of p-methoxybenzyl groups.

Secondary amines: Synthesis and effect of length of spacer linking two phenyl rings on biological activity

N-Benzyl benzylamines (1a-11a) and N-benzyl anilines (1b-11b) were synthesized by sodium borohydride reduction of aldimines of benzylamine and aniline respectively. The products were characterized on the basis of elemental analysis and spectral studies and screened for antifungal potential against four fungi and evaluated for nematicidal activity against two nematodes. The former compounds were found to be more effective as compared to the latter thus indicating an enhancement of biological activity due to introduction of an extra methylene group between two phenyl rings of aromatic secondary amines.