3682-71-1

Basic information

• Product Name: 2-phenylindazole
• Synonyms: 2-phenylindazole;2-PHENYL-2H-INDAZOLE
• CAS NO: 3682-71-1
• Molecular Formula: C₁₃H₁₀N₂
• Molecular Weight: 194.2319
• Mol File: 3682-71-1.mol
• Article Data: 69

Chemical Properties

• Melting Point: 81-82 °C
• Boiling Point: 178-182 °C(Press: 6 Torr)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• PKA: 0.16±0.30(Predicted)
• CAS DataBase Reference: 2-phenylindazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylindazole(3682-71-1)
• EPA Substance Registry System: 2-phenylindazole(3682-71-1)

Safety Data

• Hazardous Substances Data: 3682-71-1(Hazardous Substances Data)

Usage

General Description

2-phenylindazole, also known as indazolone, is a chemical compound with a molecular formula C14H11N. It is a heterocyclic aromatic organic compound containing a benzene ring fused to an indazole ring. 2-phenylindazole is used in the synthesis of pharmaceuticals, agrochemicals, and organic materials. It has been studied for its potential therapeutic applications, including as an anti-inflammatory, analgesic, and anti-cancer agent. Additionally, 2-phenylindazole has been found to have antioxidant and antiviral properties. 2-phenylindazole is of interest to researchers and industries for its diverse potential uses and biological activities.

Upstream product

• 137720-83-3 (E)-2-(phenyldiazenyl)phenylmethanol 
• 32286-81-0 2-phenyl-4,5,6,7-tetrahydro-2H-indazole 
• 60109-75-3 2-phenylindazoline 
• 1624-50-6 (Ε)-N-(2-nitrobenzylidene)aniline 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 6269-45-0 2-(2-nitrophenyl)benzo[d]thiazole 
• 100-63-0 phenylhydrazine 
• 251982-42-0 methyl 2-phenyl-2H-indazole-3-carboxylate 
• 271-44-3 benzimidazole 
• 98-80-6 phenylboronic acid 
• 262364-62-5 1-o-bromobenzyl-1-phenylhydrazine 
• 10359-18-9 N-(4-nitrobenzyl)aniline 
• 6319-21-7 2-(hydroxymethyl)azobenzene 
• 70704-39-1 3-chloro-2-phenyl-2H-indazole 

Downstream Products

• 61063-06-7 7-nitro-2-phenyl-2H-indazole 
• 60109-75-3 2-phenylindazoline 
• 3682-56-2 2-phenylazo-benzoic acid 
• 1433849-46-7 1-methyl-2-phenyl-1H-indazole-3(2H)-thione 
• 1415021-81-6 phenyl-(2-phenyl-2H-indazol-3-yl)methanone 
• 30764-40-0 1-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propan-2-one 
• 7031-95-0 1-benzoxy-2,2,6,6-tetramethylpiperidine 
• 1415021-91-8 (4-methoxyphenyl)(2-phenyl-2H-indazol-3-yl)methanone 

Relevant articles and documents

Synthesis and Antitumor Activity Evaluation of Cyclometalated 2H-Indazole Ruthenium(II) and Iridium(III) Complexes

In this work, a series of novel C?N cyclometalated 2H-indazole Ru(II) and Ir(III) complexes were synthesized, wherein chelating ligands with substituents like H, and isopropyl group in the R4 position of the phenyl ring of the 2H-indazole chela

Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of N-(2-nitroarylidene)amines

Ionic diamine rhodium complexes catalyze the reductive N-heterocyclization of N-(2-nitroarylidene)amines under carbon monoxide to afford the corresponding 2H-indazoles in up to 75% yields.

Direct Formation of 2-Substituted 2 H-Indazoles by a Pd-Catalyzed Reaction between 2-Halobenzyl Halides and Arylhydrazines

A direct and operationally simple method for the regioselective synthesis of 2-aryl-substituted 2H-indazoles is reported. The Pd-catalyzed reaction between easily available 2-bromobenzyl bromides and arylhydrazines employing Cs2CO3 as the base and t-Bu3PHBF4 as the ligand in DMSO at 120 °C in a sealed tube delivers the 2-substituted-2H-indazoles in a single synthetic step with yields up to 79%. The new method is based on a regioselective intermolecular N-benzylation followed by intramolecular N-arylation and oxidation.

Manganese-Catalyzed Electrochemical Tandem Azidation-Coarctate Reaction: Easy Access to 2-Azo-benzonitriles

A one-pot cascade transformation consisting of an electrochemically driven azidation of 2H-indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.

Design, synthesis and anticandidal evaluation of indazole and pyrazole derivatives

Candidiasis, caused by yeasts of the genus Candida, is the second cause of superficial and mucosal infections and the fourth cause of bloodstream infections. Although some antifungal drugs to treat candidiasis are available, resistant strains to current therapies are emerging. Therefore, the search for new candicidal compounds is certainly a priority. In this regard, a series of indazole and pyrazole derivatives were designed in this work, employing bioisosteric replacement, homologa-tion, and molecular simplification as new anticandidal agents. Compounds were synthesized and evaluated against C. albicans, C. glabrata, and C. tropicalis strains. The series of 3-phenyl-1H-indazole moiety (10a–i) demonstrated to have the best broad anticandidal activity. Particularly, compound 10g, with N,N-diethylcarboxamide substituent, was the most active against C. albicans and both miconazole susceptible and resistant C. glabrata species. Therefore, the 3-phenyl-1H-indazole scaf-fold represents an opportunity for the development of new anticandidal agents with a new chemo-type.