16778-51-1

Basic information

• Product Name: 1-(4-nitrophenyl)-1H-indazole
• Synonyms: 1-(4-nitrophenyl)-1H-indazole
• CAS NO: 16778-51-1
• Molecular Weight: 239.233
• Mol File: 16778-51-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1-(4-nitrophenyl)-1H-indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-nitrophenyl)-1H-indazole(16778-51-1)
• EPA Substance Registry System: 1-(4-nitrophenyl)-1H-indazole(16778-51-1)

Safety Data

• Hazardous Substances Data: 16778-51-1(Hazardous Substances Data)

Usage

General Description

1-(4-nitrophenyl)-1H-indazole, also known as 4-Nitrophenyl-1H-indazole, is a chemical compound with the molecular formula C13H9N3O2. It is a derivative of indazole, a heterocyclic aromatic organic compound. This chemical is commonly used in the pharmaceutical and chemical industries as a building block for the synthesis of various organic compounds, including pharmaceutical drugs, agrochemicals, and dyes. It has also been studied for its potential biological activities, including its role as an anticancer and antimicrobial agent. Additionally, 1-(4-nitrophenyl)-1H-indazole has been investigated for its potential use as a fluorescent dye in analytical and biological assays. Overall, this compound has a range of potential applications and is an important intermediate in organic synthesis and pharmaceutical research.

Upstream product

• 271-44-3 benzimidazole 
• 100-25-4 para-dinitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 13436-48-1 1-methyl-1H-indazole 
• 586-78-7 para-nitrophenyl bromide 
• 350-46-9 4-Fluoronitrobenzene 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 1330064-46-4 C₂₁H₁₄ClF₃N₄O 

Relevant articles and documents

A post-synthetically modified metal-organic framework for copper catalyzed denitrative C-N coupling of nitroarenes under heterogeneous conditions

Here we report, for the first time, the Ullmann C-N coupling reaction of nitroarenes which is achieved by using a copper containing metal-organic framework (MOF) catalyst under heterogenous conditions. The ready availability of nitroarenes and their low cost have made them ideal replacements for haloarenes as electrophilic coupling partners. Notably, the reaction protocol suppresses the by-product formation in the catalytic reaction. The catalyst has been designed and synthesized by two step post-synthesis functionalization of a MOF,viz.dabco MOF-1 with a -NH2functional group (DMOF-NH2). In the post-synthetic treatment, salicylaldehyde has been used for organic modification first and then copper(ii) was successfully incorporated onto the inner surface of the porous material. The hybrid porous solid thus obtained has been employed in the catalytic C-N coupling reaction of nitroarenes with a wide variety of amines under heterogeneous conditions, which displayed very high turnover frequencies (TOF) in catalytic reactions attesting its efficacy towards theN-arylation reaction.

Integrating CuO?Fe2O3 Nanocomposites and Supramolecular Assemblies of Phenazine for Visible-Light Photoredox Catalysis

A photoredox catalytic ensemble consisting of CuO-Fe2O3 nanocomposites and oligomeric derivative of phenazine has been developed. The prepared system acts as an efficient photoredox catalyst for C?N bond formation reaction via SET mechanism under ‘green’ conditions (aerial environment, mixed aqueous media, recyclable), requiring less equivalents of base and amine substrate. The present study demonstrates the significant role of supramolecular assemblies as photooxidants and reductants upon irradiation and their important contribution towards the activation of the metallic centre through energy transfer and electron transfer pathways. The potential of oligomer 4: CuO-Fe2O3 has also been explored for C?C bond formation reactions via the Sonogashira protocol.

N-Picolinamides as ligands for Ullmann-type C-N coupling reactions

The use of N-phenyl-2-pyridincarboxamide-1-oxide as a ligand with Cu2O in Ullmann type C-N bond formations between aryl halides and N-heteroaryls in common solvents, such as MeCN, DMF, and DMSO at 82-120 °C has been successfully demonstrated. The ligand is effective when only 4% equiv is used relative to the substrate. The reaction provided the corresponding products in coupling of electron-rich, electron poor, and ortho-substituted aryl halides, including ortho aryl-chlorides, in good to very good yields. N-arylation is selectively preferred at the benzyl position when ortho-halide benzyl bromide is reacted with one equivalent of pyrazole. However, di-N-arylation is achieved in very high yields when 2.5 equiv of pyrazole is used, providing a stoichiometric control over the coupling reaction.