6373-46-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxyaniline is used as an intermediate in the synthesis of Acetaminophen-d3, the labeled analogue of Acetaminophen (A161220), which is an analgesic and antipyretic agent. This intermediate plays a crucial role in the production of this widely used pain reliever and fever reducer.
Used in Chemical Research:
4-Benzyloxyaniline can be used to prepare N-(4-phenoxyphenyl)benzenesulfonamide derivatives, which have potential applications as antagonists for the nonsteroidal progesterone receptor. This makes it a valuable compound for researchers working on the development of new drugs targeting hormone receptors and related therapeutic applications.

InChI:InChI=1/C13H13NO/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9H,10,14H2

Upstream product

• 1145-76-2 benzyl 4-nitrophenyl ether 
• 100-02-7 4-nitro-phenol 
• 100-39-0 benzyl bromide 
• 852668-28-1 (4-benzyloxyphenyl)carbamic acid tert-butyl ester 
• 94040-95-6 1-azido-4-(benzyloxy)benzene 
• 588-53-4 4-benzylidenamino-phenol 
• 58750-86-0 N-(4-(benzyloxy)phenyl)-4-methylbenzenesulfonamide 
• 371-40-4 4-fluoroaniline 
• 100-51-6 benzyl alcohol 
• 6793-92-6 p-benzyloxyphenylbromide 
• 146631-00-7 [4-(benzyloxy)phenyl]boronic acid 
• 100-44-7 benzyl chloride 
• 123-30-8 4-amino-phenol 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 

Downstream Products

• 96068-66-5 N,N'-bis-(4-benzyloxy-phenyl)-thiourea 
• 139768-71-1 4-benzyloxyphenyl isothiocyanate 
• 861541-25-5 N,N'-bis-(4-benzyloxy-phenyl)-formamidine 
• 19514-92-2 N-[4-(benzyloxy)phenyl]-2-chloroacetamide 
• 102883-55-6 (4-benzyloxy-phenyl)-amidophosphoric acid diphenyl ester 
• 20012-18-4 N,N-bis(2-hydroxyethyl)-3-benzyloxyaniline 
• 20878-58-4 2-(p-Benzyloxy-phenyl-carbamoyl)-anilin 
• 103271-60-9 4-Benzyloxyanilid der Bis-(4-acetoxy-phenyl)-essigsaeure 
• 57181-12-1 ethyl 2-chloro-3-(4-benzyloxyphenyl)propionate 
• 57666-87-2 5-(p-benzyloxyphenyl)-2-furaldehyde 
• 77725-90-7 4-(p-benzyloxyphenyl)aminoquinazoline 
• 115891-06-0 2-(4-Benzyloxy-phenylamino)-nicotinic acid 
• 117901-12-9 N-(benzyloxy-4 phenyl) <(tert.butoxycarbonyl) amino>-2 hydroxy-3 propionamide (2-S) 
• 80548-06-7 ethyl α-benzamido-β-acrylate 

Relevant academic research and scientific papers

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Structure based design, synthesis, and biological evaluation of imidazole derivatives targeting dihydropteroate synthase enzyme

In this study, we have designed and synthesized 2-((5-acetyl-1-(phenyl)-4-methyl-1H-imidazol-2-yl)thio)-N-(4-((benzyl)oxy)phenyl) acetamide derivatives. Antimicrobial activities of all the imidazole derivatives have been examined against Gram-positive and Gram-negative bacteria and results showed that the conjugates have appreciable antibacterial activity. Besides, several analogous were evaluated for their in vitro antiresistant bacterial strains such as Extended-spectrum beta-lactamases (ESBL), Vancomycin-resistant Enterococcus (VRE), and Methicillin-resistant Staphylococcus aureus (MRSA). The SAR revealed that the 12l compound resulted in potency against all bacterial strains as well as ESBL, VRE, and MRSA strains. Lipinski's rule of five, and ADME studies were preformed for all the synthesized compounds with Staphylococcus aureus dihydropteroate synthase (saDHPS) protein (PDB ID: 6CLV) and were found standard drug-likeness properties of conjugates. Moreover, the binding mode of the ligands with the protein study has been examined by molecular docking and results are quite promising. Besides, all the analogous were tested for their in vitro antituberculosis, antimalarial, and antioxidant activity.

Danshensu derivativeS as well as preparation method and medical application thereof

The invention discloses Danshensu derivatives as well as a preparation method and medical application thereof. The derivatives have a general structure as shown in a general formula (I) shown in the specification, wherein R1 represents OH or OCH3; R2 represents H or Ac; and R3 represents a first structure, a second structure or a third structure shown in the specification. Compared with a raw material medicine, the derivatives synthesized by the invention have the advantages that the fat solubility is increased, so that the derivatives can penetrate through the blood-brain barrier (BBB), the medicine stability is greatly improved, and the curative effect is further improved. Therefore, the derivatives disclosed by the invention can be applied to preparation of drugs for preventing, treating, treating and/or reducing the cerebral infarction volume of a patient, improving the balance coordination ability of the patient and other diseases, and a new therapeutic drug is provided for preventing and treating cerebrovascular or cranial nerve diseases.

Triphenylamine- And triazine-containing hydrogen bonded complexes: liquid crystalline supramolecular semiconductors

Despite the fact that triphenylamine derivatives have been widely explored as hole-transporting materials, studies on charge transport properties in the liquid crystal phase have been overlooked. Here, it is reported that triphenylamine liquid crystals can attain very high hole mobility values in a hexagonal columnar mesophase, up toμ≈ 5 cm2V?1s?1. The columnar liquid crystalline phase was obtained by a proper design of a supramolecular mesogen, and this is unprecedented for triphenylamine liquid crystals. In fact, the supramolecules were formed by hydrogen-bonded 1?:?3 complexes of a star-shaped triazine core and three triphenylamine peripheral units. The resulting hexagonal columnar mesophase acts as a successful scaffold that confines TPA units at the periphery of columns. Challenging DFT theoretical investigations into a model based on such supramolecular systems involving a large number of atoms were undertaken to explore the stability and geometry of the complexes and their electronic properties.

Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal

The reduction of nitroaromatic compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, we report for the first time the use of gallium metal as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quantitative yields with short reaction times of 10-60 minutes.

Applicability of aluminum amalgam to the reduction of arylnitro groups

An array of arylnitro compounds with various functionality were treated with freshly-prepared aluminum amalgam in THF/water solution and resulted in the corresponding arylamines. The Al(Hg)-mediated reductions are relatively rapid with consumption of the amalgam and disappearance of starting material occurring over 20–30 min. The workup of the reductions involves only removal of the insoluble by-products by filtration followed by concentration. Only in some cases is chromatography required to secure the pure product. The desired arylamines are furnished in quantities of 25–100 mg, which in some cases, could be taken on to the next reaction without further purification. Reductions of 4-nitrobenzyl derivatives of carbohydrates or nucleosides were selective in affording the corresponding 4-aminobenzyl products. To show applicability in click chemistry, selected aminobenzyl products are directly azidated to yield products that were then used in click reactions to afford the corresponding 1,2,3-triazoles.

Development of Carbon-Neutral Cellulose-Supported Heterogeneous Palladium Catalysts for Chemoselective Hydrogenation

Palladium catalysts immobilized on cellulose particles (Pd/CLP) and on a cellulose-monolith (Pd/CLM) were developed. These composites were applied as hydrogenation catalysts and their catalyst activities were evaluated. Although both catalysts catalyzed the deprotection of benzyloxycarbonyl-protected aromatic amines (Ar-N-Cbz) and aromatic benzyl esters (Ar-CO2Bn), only Pd/CLM could accomplish the hydrogenolysis of aliphatic-N-Cbz and aliphatic-CO2Bn protective groups. The difference in the physical structure of the cellulose supports induced unique chemoselectivity. Aliphatic-N-Cbz and aliphatic-CO2Bn groups were tolerated under the Pd/CLP-catalyzed hydrogenation conditions, while Ar-N-Cbz, Ar-CO2Bn, alkene, alkyne, azido and nitro groups could be smoothly reduced.

AGRICULTURAL CHEMICALS

The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.