14429-02-8

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl[(4-methoxyphenyl)methyl]amine is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with unique therapeutic properties.
Used in Organic Compounds Synthesis:
It is utilized as a key component in the synthesis of organic compounds, where its specific structure can be leveraged to create novel molecules with potential applications in various fields.
Used in Medicinal Chemistry:
Benzyl[(4-methoxyphenyl)methyl]amine is employed as a building block in medicinal chemistry, where its unique structure can be used to design and develop new therapeutic agents with improved efficacy and selectivity.
Used in Drug Development:
It serves as a valuable compound in drug development, potentially leading to the discovery of new drugs with innovative mechanisms of action and enhanced pharmacological profiles.

Upstream product

• 622-72-0 N-(4-methoxylbenzylidene)benzylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-46-9 benzylamine 
• 31490-38-7 N-(4-methoxybenzyl)benzaldimine 
• 130517-94-1 (E)-N-benzyl-1-(4-methoxyphenyl)methanimine 
• 100-39-0 benzyl bromide 
• 2393-23-9 4-methoxy-benzylamine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 171414-22-5 N-Benzyl-N-(4-methoxy-benzyl)-4-nitro-benzenesulfonamide 
• 171414-18-9 N-Benzyl-N-(4-methoxy-benzyl)-2-nitro-benzenesulfonamide 
• 100-51-6 benzyl alcohol 
• 623-03-0 4-Cyanochlorobenzene 
• 100-47-0 benzonitrile 
• 874-90-8 4-methoxybenzonitrile 

Downstream Products

• 145126-73-4 1-butyl-2-(ethoxycarbonyl)-N-benzyl-N-(p-methoxybenzyl)aziridine-2-carboxamide 
• 1027243-08-8 (1R,2S)-2-Hydroxymethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide 
• 208344-72-3 (1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide 
• 208344-73-4 (1R,2S,3R)-2-Hydroxymethyl-3-methyl-cyclopropanecarboxylic acid benzyl-(4-methoxy-benzyl)-amide 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 2393-23-9 4-methoxy-benzylamine 
• 100-46-9 benzylamine 
• 656223-60-8 (S)-N-benzyl-N-(p-methoxybenzyl)(cyclohex-2-enyl)amine 
• 527751-10-6 (S)-N-benzyl-(cyclohex-2-enyl)amine 
• 1010438-19-3 N-benzyl-N-octyl-4-methoxybenzylamine 
• 1010438-23-9 N-benzyl-N-(3-methylbutyl)-4-methoxybenzylamine 

Relevant academic research and scientific papers

Application of odorless thiols for the cleavage of 2- and 4-nitrobenzenesulfonamides

Several odorless or faint-smelling thiols were tested to cleave 2- and 4-nitrobenzenesulfonyl groups, which are widely utilized for selective protection and activation of amines. p-Mercaptobenzoic acid (7) was found to be the most useful thiol for cleavin

Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines

Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.

Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions

A simple and efficient copper-catalyzed selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines with an oxazaborolidine-BH3 complex is reported. The selectivity control was achieved under mild conditions by switching the solvent and the copper catalysts. More than 30 primary amine-boranes and 40 secondary amines were synthesized via this strategy in high selectivity and yields of up to 95%. The strategy was applied to the synthesis of 15N labeled in 89% yield.

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane

Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.

Synthesis, characterization, and antibacterial activity of dibenzildithiocarbamate derivates and Ni(II)–Cu(II) coordination compounds

In this work, the study of the synthesis methodology to obtain dibenzylamine derivates as intermediates for the formation of dithicarbamate ligands (DTC) and its coordination compounds was conducted. Four molecules derived from dibenzylamine were synthesized by two methodologies: classical (reflux) and microwave. From these amines, Four dithiocarbamate ligands (DTC): dibenzyldithiocarbamate, N-benzyl-1-(4-methoxyphenyl)dithiocarbamate, N-benzyl-1-(4-chlorophenyl)dithiocarbamate, and N-benzyl-1-(3-nitrophenyl)dithiocarbamate, and eight coordination complexes with general formula [M(DTC)2]nH2O (M= Cu(II) and Ni(II)) were obtained. All the compounds were characterized using different spectroscopic and thermal techniques such as Fourier-transform infrared spectroscopy (FT-IR), ultraviolet–visible spectroscopy (UV–VIS), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), thermogravimetric analysis–differential scanning calorimetry (TGA-DSC). Additionally, it was possible to characterize two new crystalline phases of salts through single-crystal X-ray diffraction: dibenzyl ammonium nitrate and N-benzyl-1-(3-nitrophenyl)ammonium chloride. Additionally, microbial inhibition tests were conducted using the dibenzildithiocarbamate derivates. All DTC compounds showed important activity against Pseudomonas aeruginosa and Staphylococcus aureus but less sensitivity against Escherichia coli and Mycobacterium smegmatis. Among the coordination compounds, only [Cu(N-benzyl-1-(3-nitrophenyl)dithiocarbamate)2] presented a moderate activity against M. smegmatis mc2 155.

Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones

We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita

Exploiting Configurational Lability in Aza-Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides

Methods for establishing the absolute configuration of sulfur-stereogenic aza-sulfur derivatives are scarce, often relying on cumbersome protocols and a limited pool of enantioenriched starting materials. We have addressed this by exploiting, for the first time, a feature of sulfonimidamides in which it is possible for tautomeric structures to also be enantiomeric. Such sulfonimidamides can readily generate prochiral ions, which we have exploited in an enantioselective alkylation process. Selectivity is achieved using a readily prepared bis-quaternized phase-transfer catalyst. The overall process establishes the capability of configurationally labile aza-sulfur species to be used in asymmetric catalysis.

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.

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.