1145-76-2

Basic information

• Product Name: 1-BENZYLOXY-4-NITROBENZENE
• Synonyms: 4-BENZYLOXY-1-NITROBENZENE;1-BENZYLOXY-4-NITROBENZENE;BENZYL (4-NITROPHENYL) ETHER;AURORA 19374;4-Benzyloxynitrobenzene;Benzene, 1-nitro-4-(phenylmethoxy)-;Benzyl p-nitrophenyl ether;Ether, benzyl p-nitrophenyl
• CAS NO: 1145-76-2
• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.23
• EINECS: 214-545-9
• Mol File: 1145-76-2.mol
• Article Data: 68

Chemical Properties

• Melting Point: 105.0 to 109.0 °C
• Boiling Point: 386.2°C at 760 mmHg
• Flash Point: 176°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 7.99E-06mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-BENZYLOXY-4-NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYLOXY-4-NITROBENZENE(1145-76-2)
• EPA Substance Registry System: 1-BENZYLOXY-4-NITROBENZENE(1145-76-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 1145-76-2(Hazardous Substances Data)

Usage

General Description

1-Benzyloxy-4-nitrobenzene is a chemical compound with the molecular formula C13H11NO3. It is a yellow crystalline solid that is primarily used in organic synthesis as a building block for various compounds, particularly in the pharmaceutical industry. It is synthesized by the nitration of 1-benzyloxy-4-nitrobenzene with a mixture of sulfuric and nitric acids. 1-Benzyloxy-4-nitrobenzene is an important intermediate for the production of various pharmaceuticals, dyes, and other organic compounds. It is important to handle 1-benzyloxy-4-nitrobenzene with care as it is toxic and can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C13H11NO3/c15-14(16)12-6-8-13(9-7-12)17-10-11-4-2-1-3-5-11/h1-9H,10H2

Upstream product

• 3871-20-3 tris(p-nitrophenyl)phosphate 
• 100-39-0 benzyl bromide 
• 100-02-7 4-nitro-phenol 
• 108-88-3 toluene 
• 3002-48-0 tetra-n-butylammonium p-nitrophenoxide 
• 905718-45-8 [(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate] 
• 100-51-6 benzyl alcohol 
• 87100-28-5 pinacol benzylboronate 
• 616-38-6 carbonic acid dimethyl ester 
• 25316-59-0 benzyl tri-n-butylammonium bromide 
• 350-46-9 4-Fluoronitrobenzene 
• 5197-95-5 benzyltriethylammonium bromide 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 6373-46-2 p-benzyloxyaniline 
• 123-30-8 4-amino-phenol 
• 101653-61-6 4,4-bis(phenylmethoxy)azoxybenzene 
• 4279-47-4 (2,4-dinitro-phenyl)-(4-nitro-benzyl)-ether 
• 861319-93-9 (2,4-dinitro-phenyl)-(2-nitro-benzyl)-ether 
• 52068-30-1 4-benzyloxyphenylhydrazine hydrochloride 
• 221229-92-1 ethyl 8-(benzyloxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate 
• 385446-23-1 N-(4-(benzyloxy)phenyl)-1-phenylmethanimine 

Relevant articles and documents

The Nucleophilic Ring-opening of N-Benzylquinuclidinium Bromide

N-Benzylquinuclidinium bromide was ring opened by a series of heteronucleophiles, in the presence of cesium carbonate, to yield the corresponding N-benzyl-4-(2-hetero-ethyl)piperidines. The best yields were found with thiophenol (56%), phenol (55%), and benzimidazole (38%) as nucleophiles.

Ionic liquid as an efficient promoting medium for two-phase nucleophilic displacement reactions

The use of the room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate as an efficient catalyst and solvent for several representative nucleophilic substitution reactions under aqueous-RTIL phase transfer conditions was explored. Recycling and reuse of the reaction medium was demonstrated for the azide formation.

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DEMETHYLATION STUDIES. IV. THE IN VITRO AND IN VIVO CLEAVAGE OF ALKYL-

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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.

Application of iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds

The invention discloses an application of an iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds, and particularly relates to a method for synthesizing corresponding aryl benzyl ether compounds by taking di-tert-butyl peroxide as an oxidizing agent and carrying out oxidative coupling reaction on phenolic compounds and toluene compounds. According to the method, the iron (III) complex is used as the catalyst for the first time, and oxidative coupling of the phenolic compound and the toluene compound is realized. The method is the first oxidative coupling reaction of phenolic compounds and benzyl C(sp3)-H bonds, and a new method is provided for synthesizing aryl benzyl ether compounds. Compared with an existing synthesis method, the method provided by the invention avoids using toxic and polluting halogenated hydrocarbon and strong base, has better atom economy, and conforms to the development concept of green synthetic chemistry.

Design, synthesis and evaluation of tetrahydrocarbazole derivatives as potential hypoglycemic agents

Two series of tetrahydrocarbazole derivatives have been designed and synthesized based on ZG02, a promising candidate developed in our previous studies. The newly prepared compounds were screened for glucose consumption activity in HepG2 cell lines. Aza-tetrahydrocarbazole compound 12b showed the most potent hypoglycemic activity with a 45% increase in glucose consumption when compared to the solvent control, which had approximately 1.2-fold higher activity than the positive control compounds (metformin and ZG02). An investigation of the potential mechanism indicated that 12b may exhibit hypoglycemic activity via activation of the AMPK pathway. Metabolic stability assays revealed that 12b showed good stability profiles in both artificial gastrointestinal fluids and blood plasma from SD rats. An oral glucose tolerance test (OGTT) was performed and the results further confirmed that 12b was a potent hypoglycemic agent.