355815-47-3

Usage

Uses

Used in Pharmaceutical Industry:
(4-FLUORO-BENZYL)-(4-METHOXY-BENZYL)-AMINE is used as a building block for the synthesis of various pharmaceuticals due to its ability to contribute to the development of biologically active molecules. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (4-FLUORO-BENZYL)-(4-METHOXY-BENZYL)-AMINE serves as a reagent for the preparation of complex organic compounds. Its distinct reactivity aids in the synthesis process, facilitating the creation of specialty chemicals with specific properties and uses.
Used in Research and Development:
(4-FLUORO-BENZYL)-(4-METHOXY-BENZYL)-AMINE is utilized as a starting material in research and development for the design and synthesis of new compounds. Its versatility as a chemical building block is crucial for exploring novel chemical spaces and discovering innovative applications in various industries.

InChI:InChI=1/C15H16FNO/c1-18-15-8-4-13(5-9-15)11-17-10-12-2-6-14(16)7-3-12/h2-9,17H,10-11H2,1H3/p+1

Upstream product

• 105482-69-7 N-(4-fluorobenzyl)(4-methoxyphenyl)methanimine 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 159979-96-1 4-fluorobenzyl azide 
• 1194-02-1 4-fluorobenzonitrile 
• 2393-23-9 4-methoxy-benzylamine 
• 140-75-0 para-fluorobenzylamine 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 24941-76-2 1-fluoro-4-(4-methoxyphenethyl)benzene 

Relevant academic research and scientific papers

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.

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.

One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt-Fe3O4nanoparticle catalyst

We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt-Fe3O4 nanoparticle (NP) catalyst. The use of a bimetallic catalyst resulted in enhanced reactivity and selectivity compared to that of either monometallic Pd-Fe3O4 or the Pt-Fe3O4 NP catalyst. Using this bimetallic catalytic system, we were successful in the synthesis of various unsymmetrical secondary amines under mild conditions. However, aryl nitriles containing an electron-donating substituent were rather resistant to the reductive amination, and when hexafluoroisopropanol (HFIP) was used as a co-solvent, the reaction selectivity and yield for unsymmetrical secondary amines increased dramatically. Using the catalyst system, one-pot, gram-scale synthesis of indole was possible from 2-nitrophenylacetonitrile. Due to the magnetic property of the Fe3O4 support, the bimetallic catalyst could easily be recycled using an external magnet at least four times.

Heterogeneous AgPd Alloy Nanocatalyst for Selective Reduction of Aromatic Nitro Compounds Using Formic Acid as Hydrogen Source

Abstract: A Heterogeneous catalyst developed for selective reduction of nitroarenes to the analogous anilines using formic acid as hydrogen source. This catalytic procedure offers a simplistic path to prepare aromatic amines in good to excellent yields. Especially, even anilines functionalized with other potentially reducible moieties are obtained with high selectivity. Herein, we report convenient and stable bimetallic AgPd nanocatalyst supported on metal organic framework coated with polyaniline. Hydrogenation of nitroarenes gave analogues anilines with excellent yields at 90?°C in 6?h with no use of additives. Catalyst maintained stable performance in five repeated cycles. Graphic Abstract: [Figure not available: see fulltext.].

Iron-Catalyzed Intramolecular C-H Amination of α-Azidyl Amides

Iron-catalyzed intramolecular C-H amination of aliphatic azides has recently emerged as a powerful tool for the preparation of nitrogen heterocycles. This paper reports that α-azidyl amides can be converted in high efficacy to imidazolinone compounds via intramolecular C(sp3)-H amination by the action of a simple catalytic system composed of FeCl2 and a β-diketiminate ligand. The reactions provide a simple and atom-economical approach toward polysubstituted imidazolinones.

COMPOUNDS, SALTS THEREOF AND METHODS FOR TREATMENT OF DISEASES

The present disclosure relates to compounds according to Formula (I), treating diseases.

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.

Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent

Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.