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Usage

Uses

Used in Pharmaceutical Industry:
1-(3-nitrophenyl)-1H-1,3-benzodiazole is used as a building block in the synthesis of various organic compounds for its potential application in the development of new pharmaceuticals. Its strong electron-withdrawing properties and the presence of the benzodiazole moiety contribute to its utility in creating compounds with specific therapeutic effects.
Used in Organic Synthesis:
As a reagent, 1-(3-nitrophenyl)-1H-1,3-benzodiazole is utilized in various chemical reactions due to its electron-withdrawing nature, which can influence the reactivity and selectivity of the reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Cancer Treatment Research:
1-(3-nitrophenyl)-1H-1,3-benzodiazole is being explored for its potential use in cancer treatment. Its biological activities are under investigation to understand its effects on cancer cells and to determine if it can be developed into a therapeutic agent for cancer patients.
Used in Antimicrobial Applications:
1-(3-nitrophenyl)-1H-1,3-benzodiazole is also being studied for its antimicrobial properties, which could lead to its use in the development of new antimicrobial agents to combat resistant bacteria and other pathogens.
Used in Anti-inflammatory Research:
1-(3-nitrophenyl)-1H-1,3-benzodiazole's potential anti-inflammatory properties are being investigated, which may result in its application in the treatment of inflammatory conditions and diseases.

Upstream product

• 51-17-2 benzoimidazole 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 13331-27-6 m-nitrobenzene boronic acid 
• 585-79-5 m-nitrobromobenzene 
• 645-00-1 m-iodonitrobenzene 
• 706785-16-2 4,5-diethynyl-1-(3-nitro-phenyl)-1H-imidazole 
• 24163-36-8 3,3'-dinitrodiphenyliodonium bromide 

Downstream Products

• 1359944-44-7 N-(3-(1H-benzo[d]imidazol-1-yl)phenylcarbamothioyl)-3,4,5-trimethoxybenzamide 

Relevant academic research and scientific papers

Hypervalent iodine in synthesis 85: An efficient method for the synthesis of N-arylbenzimidazoles by the copper-catalyzed N-arylation of benzimidazole with diaryliodonium salts

A method for the synthesis of N-arylbenzimidazoles by the copper catalyzed N-arylation of benzimidazole with diaryliodonium salts was described. The process had many advantages such as mild reaction conditions, simplicity of procedure, using nonpoisonous, accessible reagents and reasonable yields. It was found that all products gave satisfactory melting points, infrared and NMR spectra.

Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water

The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.

Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions

A series of polyacrylonitrile fiber (PANF)-supported copper(II) catalysts were prepared through the immobilization of Cu(II) into prolinamide-modified PANF (PANPA-2F) and subsequently used for the synthesis of diverse N-arylimidazoles from arylboronic acids and imidazole. The prepared Cu(II)@PANPA-2Fs were well characterized by mechanical strength, FT-IR, XRD, XPS and SEM. Among them, CuCl2@PANPA-2F exhibited excellent catalytic performance, and its activity was significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.

Cu(i) based catalysts derived from bidentate ligands and studies on the effect of substituents for: N -arylation of benzimidazoles and indoles

A family of Cu(i) complexes [Cu(L1-4)(Cl)(PPh3)] (C1-C4) were synthesized from bidentate ligands L1-L4 (where L1 = (E)-2-(2-benzylidene-1-phenylhydrazinyl)pyridine, L2 = (E)-N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)aniline, L3 = (E)-2-(2

N, O-Bidentate ligand-tunable copper(II) complexes as a catalyst for Chan-Lam coupling reactions of arylboronic acids with 1 H-imidazole derivatives

An efficient procedure for Chan-Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(ii) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reac

Aromatic N-arylations catalyzed by copper-anchored porous zinc-based metal-organic framework under heterogeneous conditions

A highly porous Zn-based metal-organic framework (MOF) IRMOF-3 was covalently decorated with pyridine-2-aldehyde. The free amine group of IRMOF-3 upon condensation with pyridine-2-aldehyde affords a bidentate Schiff-base moiety in the porous matrix. The Schiff base moieties are availed to anchor copper(II) ions to display the catalyst's utility towards catalytic reactions. The catalyst was characterized by UV/Vis and IR spectroscopy, powder XRD spectrometry, SEM energy-dispersive X-ray spectrometry, and nitrogen sorption measurements. The catalyst exhibits excellent activity in catalyzing the N-arylation reaction of nitrogen-containing heterocycles with aryl bromides in DMSO medium, under mild condition (90°C) in the presence of Cs 2CO3. The porous catalyst demonstrates size selectivity towards substrate as a result of the presence of active sites inside the pores of the MOF. The anchored complex seems to be not leached or decomposed during the catalytic reactions up to five successive catalytic cycles, demonstrating practical advantages over homogeneous catalysis.

Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.

Bergman cycloaromatization of imidazole-fused enediynes: The remarkable effect of N-aryl substitution

A series of N-aryl substituted 'imidazole-fused' (Z) 3-ene-1,5-diynes was prepared and kinetic parameters for their Bergman cycloaromatization reactivities were determined. N-Arylation enhanced rates relative to N-alkyl derivatives by up to sevenfold (ANOVA p0.0001). The greatest enhancement was exhibited by the N-phenyl derivative (sevenfold at 145°C).

Ionic liquid-accelerated N-arylation of benzoazoles with diaryliodonium salts, an efficient method for the synthesis of N-aryl azoles

N-Arylation of benzoazoles with diaryliodonium salts can be performed in good yields in the room-temperature ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4), which provides an efficient method for the synthesis of N-arylbenzoazoles. The ionic liquid can be recycled and reused.

The Reaction of Some N-(Nitrophenyl)azoles with Alkali: Preparation of the Corresponding Azoxybenzenes. X-Ray Structure of 2,2'-Bis(1'',2'',4''-triazol-1''-yl)azoxybenzene

The reactions of some representative N-(nitrophenyl)azoles with boiling aqueous ethanolic potassium hydroxide solution gave the corresponding bis(azolyl)azoxybenzenes.It is deduced that, in these reactions, the N-attached azolyl groups concerned are acting as weak electron-withdrawing groups.The structure of 2,2'-bis(1'',2'',4''-triazol-1''-yl)azoxybenzene was determined in the solid state by X-ray crystallography.The monoclinic crystals belong to the space group P21/c with a 8.815(1), b 7.863(1), c 11.836(1) Angstroem, β 109.96(1) deg and Z 2.The structure was refined to an R index of 0.041 for 1172 observed terms.The midpoint of the exocyclic N=N bond lies on an inversion centre so that the azoxy oxygen is statistically distributed between two sites.The benzene ring atoms are coplanar to within experimental error, as are the triazole ring atoms, and the dihedral angle between the perpendiculars to the two rings is 35.3(3) deg.