134227-41-1

Usage

Uses

Used in Pharmaceutical Industry:
Bis(4-fluorobenzyl)aMine, 97% is used as a key intermediate in the synthesis of pharmaceuticals for its ability to form specific molecular structures that can target biological pathways.
Used in Material Science:
In the material science field, Bis(4-fluorobenzyl)aMine, 97% is utilized as a building block for the development of new materials with unique properties, such as improved stability or reactivity.
Used in Chemical Research:
As a reagent in chemical research, Bis(4-fluorobenzyl)aMine, 97% is employed for studying reaction mechanisms, exploring new synthetic routes, and developing novel chemical compounds with potential applications in various industries.

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 459-23-4 4-fluorobenzaldoxime 
• 75-07-0 acetaldehyde 
• 123-38-6 propionaldehyde 
• 123-72-8 butyraldehyde 
• 78-84-2 isobutyraldehyde 
• 428819-12-9 N-(4-fluorobenzylidene)-1-(4-fluorophenyl)methanamine 
• 2038-57-5 3-Phenylpropan-1-amine 
• 140-75-0 para-fluorobenzylamine 
• 824-75-9 p-fluorobenzamide 
• 62-53-3 aniline 
• 1194-02-1 4-fluorobenzonitrile 

Downstream Products

• 428819-12-9 N-(4-fluorobenzylidene)-1-(4-fluorophenyl)methanamine 
• 2264-12-2 1-(4-fluorobenzyl)-2-(4-fluorophenyl)-1H-1,3-benzimidazole 
• 1612866-19-9 (S)-2-(bis(4-fluorobenzyl)amino)-N-(tert-butyl)-2-phenylacetamide 
• 1612866-20-2 (R)-2-(bis(4-fluorobenzyl)amino)-N-(tert-butyl)-2-phenylacetamide 

Relevant academic research and scientific papers

Supramolecular daisy chains

Two series of self-complementary daisy chain monomers, in which a secondary ammonium ion-containing arm is grafted onto a macrocycle with either a [24]- or [25]crown-8 constitution, have been synthesized. In the solid- and 'gas'-phases, the parent [24]crown-8-based monomer forms dimeric superstructures, as revealed by X-ray crystallography and mass spectrometry, respectively. Elucidation of the complicated solution-phase behavior of this compound was facilitated by the synthesis and study of both deuterated, and fluorinated, analogues. These investigations revealed that the cyclic dimeric superstructure also dominates in solution, except when extremes of either concentration (low), temperature (high), or solvent polarity (highly polar, e.g., dimethyl sulfoxide) are employed. Whereas, upon aggregation, the [24]crown-8-based daisy chain monomers have the capacity to form stereoisomeric superstructures further complicating the study of this series of compounds. The assembly of [25]crown-8-based monomers gives only achiral superstructures. The weaker association exhibited between secondary dialkylammonium ions and crown ethers with a [25]crown-8 constitution, however, resulted in limited oligomerization-only dimeric and trimeric superstructures were formed at experimentally attainable concentrations-of [25]crown-8-based daisy chain monomers.

Effect of solvent used for crystallization on structure: Synthesis and characterization of bis(N,N-di(4-fluorobenzyl)dithiocarbamato-S,S′)M(II) (M = Cd, Hg) and usage as precursor for CdS nanophotocatalyst

Bis(N,N-di(4-fluorobenzyl)dithiocarbamato-S,S′)M(II). (M = Cd (1), Hg (2)) were prepared and fully characterized. Recrystallization of 1 from its chloroform- acetonitrile and benzene-acetonitrile solutions yielded dimeric and trimeric complex 1, respectiv

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.

Tandem Fe/Zn or Fe/In Catalysis for the Selective Synthesis of Primary and Secondary Amines?via Selective Reduction of Primary Amides

Tandem iron/zinc or iron/indium-catalysed reductions of various primary amides to amines under hydrosilylation conditions are reported under visible light activation. By a simple modification of the nature of the co-catalyst (Zn(OTf)2 vs In(OTf)3), Fe(CO)4(IMes) can promote the highly chemoselective reduction of primary amides into primary amines (21 examples, up to 93 % isolated yields) and secondary amines (8 examples, up to 51 % isolated yields), respectively. Notably, both benzamide and alkanamide derivatives can be reduced.

Platinum Nanoparticles Uniformly Dispersed on Covalent Organic Framework Supports for Selective Synthesis of Secondary Amines

Covalent organic frameworks (COFs) with pore structures are talented supports for active components. In this report, COF has been rationally fabricated and served as host for growing uniformly dispersed platinum nanoparticles with a narrow size distribution (2 nm). The obtained hybrid Pt/COF exhibits high catalytic activity in the reductive amination of benzaldehyde towards secondary amines with a yield of 96 % and good recyclability. The preferable selectivity towards secondary amines could be attributed to synergistic effects of active platinum nanoparticles and COF, in which metallic Pt nanoparticles were uniformly dispersed with a positively charged surface. This work will open an avenue towards controlling the interaction between active metals and support as well as rational design of catalysts for demanding transformations for fine agrochemicals intermediates.

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.

Chemoselective transfer hydrogenation of nitriles to secondary amines with nickel(II) catalysts

Herein we report the selective transfer hydrogenation (TH) of nitriles to secondary (2°) amines with simple Ni(II)-catalysts using ammonia borane (AB) as a source of hydrogen (H2). A bis(pyrazolylmethyl)pyridine (L1) or ethylenediamine (L4) ligated Ni(II) pre-catalyst, created in situ, could hydrogenate several aromatic- and aliphatic nitriles in full conversions and isolated yields of up to 88% under ambient temperature and in very short reaction times. Deuterium labelling experiments illustrated the incorporation of a proton on the nitrogen and hydride on the α-carbon of dibenzylamine. Using α-picoline borane, containing no dissociable protons, assisted with the postulation of a two-step TH mechanism of benzonitrile. AB was subjected to dehydrogenation and it was observed that a maximum of 2.96 equivalents of H2 gas could be generated from NiCl2?6H2O/L1.

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.

Surface modification boosts exciton extraction in confined layered structure for selective oxidation reaction

Extracting photogenerated species from bulk to surface is an essential process for gaining efficient semiconductor-based photocatalysis. However, compared with charged photogenerated carriers, neutral exciton exhibits negligible response to electric field. Accordingly, traditional strategies involving band-alignment construction for boosting directional transfer of charge carriers are impracticable for extracting bulk excitons. To this issue, we here propose that the extraction of bulk exciton could be effectively implemented by surface modification. By taking confined layered bismuth oxycarbonate (Bi2O2CO3) as an example, we highlight that the incorporation of iodine atoms on the surface could modify the micro-region electronic structure and hence lead to reduced energy of surface excitonic states. Benefiting from the energy gradient between bulk and surface excitonic states, iodine-modified Bi2O2CO3 possesses high-efficiency bulk exciton extraction, and hence exhibits promoted performance in triggering 1O2-mediated selective oxidation reaction. This work presents the positive role of surface modification in regulating excitonic processes of semiconductor-based photocatalysts. [Figure not available: see fulltext.].

Selective Synthesis of Secondary Amines from Nitriles by a User-Friendly Cobalt Catalyst

Selective hydrogenation/reductive amination of nitriles to secondary amines catalyzed by an inexpensive and user-friendly cobalt complex, (Xantphos)CoCl2, is reported. The use of (Xantphos)CoCl2 and ammonia borane (NH3?BH3) combination affords the selective reduction of nitriles to symmetrical secondary amines, whereas the employment of (Xantphos)CoCl2 and dimethylamine borane (Me2NH?BH3) along with external amines produce unsymmetrical secondary amines and tertiary amines. The general applicability of this methodology is demonstrated by the synthesis of 43 symmetrical and unsymmetrical secondary and tertiary amines bearing diverse functionalities. (Figure presented.).