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

• 32286-81-0 2-phenyl-4,5,6,7-tetrahydro-2H-indazole 
• 60418-15-7 2-(2-Azidophenyl)benzothiazole 
• 5344-90-1 2-Aminobenzyl alcohol 
• 91823-29-9 N-(2-azidobenzylidene)aniline 
• 32347-03-8 N-(2-bromobenzylidene)aniline 
• 62-53-3 aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 271-44-3 benzimidazole 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 251982-42-0 methyl 2-phenyl-2H-indazole-3-carboxylate 
• 98-80-6 phenylboronic acid 
• 137720-83-3 (E)-2-(phenyldiazenyl)phenylmethanol 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 100-63-0 phenylhydrazine 

Downstream Products

• 61063-06-7 7-nitro-2-phenyl-2H-indazole 
• 20887-06-3 N-(2-aminobenzyl)aniline 
• 1201938-12-6 3-(2-chloropyridin-4-yl)-2-phenyl-2H-indazole 
• 1201938-08-0 3-(4-chlorophenyl)-2-phenyl-2H-indazole 
• 54184-69-9 2,3-diphenyl-2H-indazole 
• 1201938-10-4 3-(3-chlorophenyl)-2-phenyl-2H-indazole 
• 1201938-09-1 2-phenyl-3-(2-methylphenyl)-2H-indazole 
• 1201938-14-8 1-(4-(2-phenyl-2H-indazol-3yl)phenyl)ethanone 
• 1201938-07-9 ethyl 4-(2-phenyl-2H-indazol-3-yl)benzoate 
• 1201938-06-8 3-(4-bromophenyl)-2-phenyl-2H-indazole 
• 1201938-13-7 3-(4-cyanophenyl)-2-phenyl-2H-indazole 
• 1201938-11-5 3-(4-nitrophenyl)-2-phenyl-2H-indazole 
• 1433849-46-7 1-methyl-2-phenyl-1H-indazole-3(2H)-thione 
• 1415021-81-6 phenyl-(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.

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.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Direct C3 Carbamoylation of 2H-Indazoles

We developed a novel method for direct C3 carbamoylation of 2H-indazoles using oxamic acids as carbamoyl radical sources. In the presence of ammonium persulfate, carbamoyl radicals were generated from oxamic acids, then used for further reactions with 2H-indazoles to afford the desired products. The reaction proceeds under metal- and catalyst-free conditions. This simple process allows for the efficient synthesis of C3 carbamoylated 2H-indazoles, which are important scaffolds in organic synthesis.