1135-12-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzylaniline is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, including:
1. 2-amino-6-benzylbenzothiazole (SKA-7): It is used in the development of drugs targeting specific diseases.
2. Ethyl 2-((4-benzylphenylamino)methylen)-malonate: It serves as a building block in the synthesis of complex organic molecules for medicinal applications.
Used in Chemical Synthesis:
4-Benzylaniline is used as a precursor in the synthesis of various chemical compounds, such as:
1. 3,5-dibromo-4-aminodiphenylmethane: It is obtained through treatment with bromine solution and can be used in the synthesis of brominated compounds with potential applications in various industries.
2. 3,5-di-iodo-4-aminodiphenylmethane: It is produced via iodination reaction using a suitable iodinating reagent, such as sodium iodate and potassium iodide, and can be used in the synthesis of iodinated compounds with potential applications in different fields.

InChI:InChI=1/C13H13N/c14-13-8-6-12(7-9-13)10-11-4-2-1-3-5-11/h1-9H,10,14H2

Upstream product

• 1817-77-2 4-benzyl-1-nitrobenzene 
• 782-92-3 1-(4-benzylphenyl)ethanone 
• 80936-82-9 4-methoxymethyl-phenylamine 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 186581-53-3 diazomethane 
• 62-53-3 aniline 
• 100-56-1 phenylmercury(II) chloride 
• 3532-25-0 N-benzyloxy benzamide 
• 33675-70-6 N-phenylacetyldiphenylamine 
• 129075-89-4 4-[(benzotriazol-1-yl)methyl]phenylamine 
• 100-58-3 phenylmagnesium bromide 
• 141883-37-6 (4-Chloro-phenyl)-(4-nitro-phenyl)-methanone oxime 
• 539-44-6 N-4-methylphenylhydrazine 
• 71-43-2 benzene 

Downstream Products

• 1823-37-6 1-benzyl-4-isocyanatobenzene 
• 101-53-1 p-benzylphenol 
• 35444-94-1 1-benzyl-4-iodobenzene 
• 76472-81-6 N-[4-(phenylmethyl)phenyl]acetamide 
• 858026-24-1 2,6-dibromo-4-phenylmethylaniline 
• 858846-51-2 4-benzyl-2,6-diiodo-aniline 
• 68723-24-0 benzoic acid-(4-benzyl-anilide) 
• 3815-28-9 4-benzyl-N-(4-nitro-benzyliden)-aniline 
• 54884-99-0 6-benzylquinoline 
• 855634-20-7 6-benzyl-4-hydroxy-quinoline-2-carboxylic acid ethyl ester 
• 37133-08-7 2-[(4-Benzyl-phenyl)-hydrazono]-malonic acid diethyl ester 
• 74649-56-2 Sodium; 3-(4-benzyl-phenyl)-2-chloro-propionate 
• 24805-59-2 diethyl {[(4-benzylphenyl)amino]methylidene}propanedioate 
• 218297-71-3 3-(4-Benzyl-phenylamino)-propionic acid ethyl ester 

Relevant academic research and scientific papers

Pyrrolic nitrogen-doped carbon nanotubes: Physicochemical properties, interactions with Pd and their role in the selective hydrogenation of nitrobenzophenone

Nitrogen-doped carbon nanotubes (N-CNTs) containing 63%, 73% and 80% pyrrolic-N were synthesized and used to evaluate the influence of pyrrolic nitrogen on the physicochemical properties and catalytic activity of Pd supported on N-CNTs (Pd/N-CNTs). Micrographs of Pd/N-CNTs showed that Pd was located along the defect sites of N-CNTs indicating strong Pd-support interactions. X-ray photoelectron spectroscopy revealed that the abundance of Pd0 decreased while that of Pd2+ increased as the quantity of pyrrolic nitrogen increased. The Pd2+ species were formed as Pd-N coordination complexes, which stabilized Pd2+ nanoparticles. Selective hydrogenation of nitrobenzophenone to aminobenzophenone or p-benzylaniline was used to evaluate the catalytic performance of catalysts. Pd/N-CNTs exhibited a higher selectivity towards aminobenzophenone than Pd on carbon nanotubes and Pd on activated carbon. The enhanced selectivity towards nitro-reduction alone, observed with Pd/N-CNTs was attributed to the promoting effect of pyrrolic-N. Hence, Pd/N-CNTs are promising catalysts for the selective reduction of nitro arenes.

Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper

Based on the experimental and DFT calculation results, here for the first time we built preferential adsorption sites for nitroarenes by modification of the supported Cu catalysts surface with 1,10-phenathroline (1,10-phen), by which the yield of aniline via reduction of nitroarene is enhanced three times. Moreover, a macromolecular layer was in-situ generated on supported Cu catalysts to form a stable macromolecule modified supported Cu catalyst, i.e., CuAlOx-M. By applying the CuAlOx-M, a wide variety of nitroarene substrates react smoothly to afford the desired products in up to > 99% yield with > 99% selectivity. The method tolerates a variety of functional groups, including halides, ketone, amide, and C = C bond moieties. The excellent catalytic performance of the CuAlOx-M can be attributed to that the 1,10-phen modification benefits the preferential adsorption of nitrobenzene and slightly weakens adsorption of aniline on the supported nano-Cu surface.

Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium

Primary anilines are essential building blocks to synthesize various pharmaceuticals, agrochemicals, pigments, electronic materials, and others. To date, the syntheses of primary anilines mostly rely on the reduction of nitroarenes or the transition-metal-catalyzed Ullmann, Buchwald-Hartwig and Chan-Lam cross-coupling reactions with ammonia, in which non-renewable petroleum-based chemicals are typically used as feedstocks via multiple step syntheses. A long-standing scientific challenge is to synthesize various primary anilines directly from renewable sources. Herein, we report a general method to directly convert a broad range of phenols into the corresponding primary anilines with the cheap and widely available hydrazine as both amine and hydride sources with simple Pd/C as the catalyst.

Cross-Coupling of Phenol Derivatives with Umpolung Aldehydes Catalyzed by Nickel

A nickel-catalyzed cross-coupling to construct the C(sp2)-C(sp3) bond was developed from two sustainable biomass-based feedstocks: phenol derivatives with umpolung aldehydes. This strategy features the in situ generation of moisture/air-stable hydrazones from naturally abundant aldehydes, which act as alkyl nucleophiles under catalysis to couple with readily available phenol derivatives. The avoidance of using both halides as the electrophiles and organometallic or organoboron reagents (also derived from halides) as the nucleophiles makes this method more sustainable. Water tolerance, great functional group (ketone, ester, free amine, amide, etc.) compatibility, and late-stage elaboration of complex biological molecules exemplified its practicability and unique chemoselectivity over organometallic reagents.

Nickel-catalyzed cross-coupling of aldehydes with aryl halides: Via hydrazone intermediates

Traditional cross-couplings require stoichiometric organometallic reagents. A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed, merging the Wolff-Kishner reduction and the classical cross-coupling reactions. Aromatic aldehydes, aryl iodides and aryl bromides are especially effective in this new cross-coupling chemistry.

Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors

Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42?nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.

N-(4-substituted phenyl)-2-substituted acetamide compound and is use as SIRT2 protein inhibitor

The invention discloses a compound shown in the formula I or its pharmaceutically acceptable salt, crystalline form and solvate. X represents a group shown in the description, Y represents a group shown in the description, R1, R2 and R3 independently represent H, hydroxyl, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or phenyl, and R4 represents aryl, heteroaryl, substituted aryl or substituted heteroaryl. The novel compound shown in the formula I has good inhibition activity to SIRT2 and tumors, has a good medicinal value and provides a novel potential choice for clinical medication.

Palladium- and nickel-catalyzed cross-couplings of unsaturated halides bearing relatively acidic protons with organozinc reagents

(Chemical Equation Presented) A wide range of polyfunctional aryl, heteroaryl, alkyl, and benzylic zinc reagents were coupled with unsaturated aryl halides bearing an acidic NH or OH proton, using Pd(OAc)2 (1 mol %) and S-Phos (2 mol %) as catalyst without the need of protecting groups. A similar nickel-catalyzed reaction is described. The relative kinetic basicity of organozinc compounds as well as their stability toward acidic protons is also described.

New method for the reduction of benzophenones with Raney Ni-Al alloy in water

Raney Ni-Al alloy in a dilute alkaline aqueous solution has been shown to be a powerful reducing agent, which is highly effective in the reduction of benzophenones to the corresponding hydrocarbon derivatives, in the absence of any organic solvents. Copyright Taylor & Francis Group, LLC.

Substituted indolines which inhibit receptor tyrosine kinases

Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.