27692-74-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-(4-PYRIDYLMETHYL)ANILINE is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its chemical properties and reactivity.
Used in Dye and Pigment Production:
In the dye and pigment industry, 4-(4-PYRIDYLMETHYL)ANILINE is utilized as an intermediate, playing a crucial role in the creation of colorants for a wide range of applications, including textiles, plastics, and printing inks.
Used in Fine Chemicals Production:
4-(4-PYRIDYLMETHYL)ANILINE also serves as an intermediate in the production of other fine chemicals, where its unique structure and properties are leveraged to create specialty chemicals for various industrial applications.
Safety Considerations:
Given its potential mutagenic and carcinogenic properties, 4-(4-PYRIDYLMETHYL)ANILINE is used with caution, requiring proper handling and safety measures to mitigate any health risks associated with its use in research, development, and manufacturing processes.

InChI:InChI=1/C12H12N2/c13-12-3-1-10(2-4-12)9-11-5-7-14-8-6-11/h1-8H,9,13H2

Upstream product

• 2116-65-6 4-benzyl pyridine 
• 1083-48-3 4-Nitrobenzylpyridin 

Downstream Products

• 107057-55-6 N-methyl-N'-(4-[4]pyridylmethyl-phenyl)-thiourea 
• 24984-75-6 N-(4-butoxy-phenyl)-N'-(4-[4]pyridylmethyl-phenyl)-thiourea 
• 130406-99-4 1-pyrrolidinyl<4-(4-pyridylmethyl)phenyl>diazene 
• 131416-55-2 p-<(4-pyridyl)methyl>-N,N-dimethylaniline 
• 139265-32-0 4-(4-Iodo-benzyl)-1-methyl-1,2,3,6-tetrahydro-pyridine 
• 297756-63-9 1-(Z){-[4-(4-pyridinylmethyl)anilino]methylidene}-1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one 
• 297756-76-4 6-(2-Furyl)-3-{(Z)-[4-(4-pyridinylmethyl)anilino]methylidene}-1,3-dihydro-2H-indol-2-one 
• 297756-73-1 3-{(Z)-[4-(4-Pyridinylmethyl)anilino]methylidene}-6-vinyl-1,3-dihydro-2H-indol-2-one 

Relevant academic research and scientific papers

Microwave-assisted reduction of aromatic nitro compounds with novel oxo-rhenium complexes

The reduction of several aromatic nitro compounds to amines by means of the two novel catalytic systems ([IMes]2ReOBr3)/PhSiH3 and ([Py]3ReNOBr2)/PhSiH3 under microwave irradiation is here reported. These two systems were able to perform the reduction of nitro groups with higher TON and TOF when compared with previously reported systems based on oxo-rhenium core under standard heating, although they showed a lesser broad reaction scope compared with the known systems.

Cobalt nanoclusters coated with N-doped carbon for chemoselective nitroarene hydrogenation and tandem reactions in water

The development of active and selective non-noble metal-based catalysts for the chemoselective reduction of nitro compounds in aquo media under mild conditions is an attractive research area. Herein, the synthesis of subnanometric and stable cobalt nanoclusters, covered by N-doped carbon layers as core-shell (Co@NC-800), for the chemoselective reduction of nitroarenes is reported. TheCo@NC-800catalyst was prepared by the pyrolysis of the Co(tpy)2complex impregnated on Vulcan carbon. In fact, the use of a molecular complex based on six N-Co bonds drives the formation of a well-defined and distributed cobalt core-shell nanocluster covered by N-doped carbon layers. In order to elucidate its nature, it has been fully characterized by using several advanced techniques. In addition, this as-prepared catalyst showed high activity, chemoselectivity and stability toward the reduction of nitro compounds with H2and under mild reaction conditions; water was used as a green solvent, improving the previous results based on cobalt catalysts. Moreover, theCo@NC-800catalyst is also active and selective for the one-pot synthesis of secondary aryl amines and isoindolinones through the reductive amination of nitroarenes. Finally, based on diffraction and spectroscopic studies, metallic cobalt nanoclusters with surface CoNxpatches have been proposed as the active phase in theCo@NC-800material.

Commercially Available CuO Catalyzed Hydrogenation of Nitroarenes Using Ammonia Borane as a Hydrogen Source

Tandem ammonia borane dehydrogenation and nitroarenes hydrogenation has been reported as a novel strategy for the preparation of aromatic amines. However, the practical application of this strategy is subjected to the high-cost and tedious preparation of supported noble metal nanocatalysts. The commercially available CuO powder is herein demonstrated to be a robust catalyst for hydrogenation of nitroarenes using ammonia borane as a hydrogen source under mild conditions. Numerous amines (even sterically hindered, halogenated, and diamines) could be obtained through this method. This monometallic catalyst is characteristic of support-free, excellent chemoselectivity, low-cost, and high recyclability, which will favor its future utilization in preparative reduction chemistry. Mechanistic studies are also carried out to clarify that diazene and azoxybenzene are key intermediates of this heterogeneous reduction.

Synthesis of water soluble Pd-Piperidoimidazolin-2-ylidene complexes and their catalytic activities in neat water

Through the strategy of water soluble N-heterocyclic carbene (NHC) ligand, Pd-catalyzed reactions were developed in aqueous media. Therefore, four new piperidoimidazolinium salts (1a-d) consisting of sulfonate (a), esther (b, c) and carboxylic acid (d) functionalities and their water-soluble Pd-NHC complexes (2a-d) were synthesized. The new compounds were characterized by elemental analysis, FTIR, TGA, UV–vis and NMR spectroscopy. The catalytic activities of water soluble Pd-NHC complexes (2a-d) were investigated using the Suzuki-Miyaura (S-M) reaction and the reduction of nitroarenes. We found that the water-soluble polar or ionic groups on piperidoimidazolin-2-ylidine had an effect on the catalytic activity. The water-soluble catalyst can be recycled efficiently and reused six times with only a very slight loss of catalytic activity.

Defect-mediated selective hydrogenation of nitroarenes on nanostructured WS2

Transition metal dichalcogenides (TMDs) are well known catalysts as both bulk and nanoscale materials. Two-dimensional (2-D) TMDs, which contain single- and few-layer nanosheets, are increasingly studied as catalytic materials because of their unique thickness-dependent properties and high surface areas. Here, colloidal 2H-WS2 nanostructures are used as a model 2-D TMD system to understand how high catalytic activity and selectivity can be achieved for useful organic transformations. Free-standing, colloidal 2H-WS2 nanostructures containing few-layer nanosheets are shown to catalyze the selective hydrogenation of a broad scope of substituted nitroarenes to their corresponding aniline derivatives in the presence of other reducible functional groups. Microscopic and computational studies reveal the important roles of sulfur vacancy-rich basal planes and tungsten-terminated edges, which are more abundant in nanostructured 2-D materials than in their bulk counterparts, in enabling the functional group selectivity. At tungsten-terminated edges and on regions of the basal planes having high concentrations of sulfur vacancies, vertical adsorption of the nitroarene is favored, thus facilitating hydrogen transfer exclusively to the nitro group due to geometric effects. At lower sulfur vacancy concentrations on the basal planes, parallel adsorption of the nitroarene is favored, and the nitro group is selectively hydrogenated due to a lower kinetic barrier. These mechanistic insights reveal how the various defect structures and configurations on 2-D TMD nanostructures facilitate functional group selectivity through distinct mechanisms that depend upon the adsorption geometry, which may have important implications for the design of new and enhanced 2-D catalytic materials across a potentially broad scope of reactions.

One-pot formic acid dehydrogenation and synthesis of benzene-fused heterocycles over reusable AgPd/WO2.72 nanocatalyst

Using nanoparticles (NPs) to catalyze multiple chemical reactions in one-pot and to achieve high-yield syntheses of functional molecules/materials is an important direction in NP chemistry, catalysis and applications. In this article, we report a nanocomposite of AgPd NPs anchored on WO2.72 nanorods (NRs) (denoted as AgPd/WO2.72) as a general catalyst for formic acid dehydrogenation and transfer hydrogenation from Ar-NO2 to Ar-NH2 that further reacts with aldehydes to form benzene-fused heterocyclic compounds. The AgPd/WO2.72 catalysis is Ag/Pd dependent and Ag48Pd52 is the most active composition for the multiple chemical reactions. The high activity of AgPd/WO2.72 arises from strong interfacial interaction between AgPd and WO2.72, resulting in AgPd lattice expansion and electron polarization from AgPd to WO2.72. The syntheses proceed in one-pot reactions among formic acid, 2-nitrophenol (or 2-nitroaniline, or 2-nitrothiophenol) and aldehydes in dioxane/water (2/1 v/v) at 80-90 °C, leading to one-pot syntheses of benzoxazoles, benzimidazoles and benzothiazoles that are key ring structures present in functional compounds for pharmaceutical, optical and polymer applications.

A capping agent dissolution method for the synthesis of metal nanosponges and their catalytic activity towards nitroarene reduction under mild conditions

We report a general strategy for the synthesis of metal nanosponges (M = Ag, Au, Pt, Pd, and Cu) using a capping agent dissolution method where addition of water to the M@BNHx nanocomposite affords the metal nanosponges. The B-H bond of the BNHx polymer gets hydrolysed upon addition of water and produces hydrogen gas bubbles which act as dynamic templates leading to the formation of nanosponges. The rate of B-H bond hydrolysis has a direct impact on the final nanostructure of the materials. The metal nanosponges were characterized using powder XRD, electron microscopy, XPS, and BET surface area analyzer techniques. The porous structure of these nanosponges offers a large number of accessible surface sites for catalytic reactions. The catalytic activity of these metal nanosponges has been demonstrated for the reduction of 4-nitrophenol where palladium exhibits the highest catalytic activity (k = 0.314 min?1). The catalytic activity of palladium nanosponge was verified for the tandem dehydrogenation of ammonia borane and the hydrogenation of nitroarenes to arylamines in methanol at room temperature. The reduction of various substituted nitroarenes was proven to be functional group tolerant except for a few halogenated nitroarenes (X = Br and I) and >99% conversion was noted within 30-60 min with high turnover frequencies (TOF) at low catalyst loading (0.1 mol%). The catalyst could be easily separated out from the reaction mixture via centrifugation and was recyclable over several cycles, retaining its porous structure.

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

A metal-organic framework-templated synthesis of γ-Fe2O3 nanoparticles encapsulated in porous carbon for efficient and chemoselective hydrogenation of nitro compounds

The γ-Fe2O3 nanoparticles well dispersed in porous carbon were fabricated via a Fe-based metal-organic framework-templated pyrolysis. The resultant product exhibits excellent catalytic activity, chemoselectivity and magnetic recyclability for the hydrogenation of diverse nitro compounds under mild conditions.

Immobilized iron oxide nanoparticles as stable and reusable catalysts for hydrazine-mediated nitro reductions in continuous flow

An experimentally easy to perform method for the generation of alumina-supported Fe3O4 nanoparticles [(6±1)nm size, 0.67 wt%]and the use of this material in hydrazine-mediated heterogeneously catalyzed reductions of nitroarenes to anilines under batch and continuous-flow conditions is presented. The bench-stable, reusable nano-Fe3O4@Al2O3 catalyst can selectively reduce functionalized nitroarenes at 1 mol% catalyst loading by using a 20 mol% excess of hydrazine hydrate in an elevated temperature regime (150°C, reaction time 2-6 min in batch). For continuous-flow processing, the catalyst material is packed into dedicated cartridges and used in a commercially available high-temperature/-pressure flow device. In continuous mode, reaction times can be reduced to less than 1 min at 150°C (30 bar back pressure) in a highly intensified process. The nano-Fe3O4@Al2O3 catalyst demonstrated stable reduction of nitrobenzene (0.5 m in MeOH) for more than 10 h on stream at a productivity of 30mmolh-1 (0.72 mol per day). Importantly, virtually no leaching of the catalytically active material could be observed by inductively coupled plasma MS monitoring.