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

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

Uses

Used in Pharmaceutical Industry:
2-phenylindazole is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic applications. It serves as an anti-inflammatory, analgesic, and anti-cancer agent, offering promising benefits in the treatment of various conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-phenylindazole is utilized as a building block in the development of new agrochemicals, contributing to the creation of innovative products that can enhance crop protection and yield.
Used in Organic Materials Industry:
2-phenylindazole is employed in the synthesis of organic materials, such as dyes, pigments, and other specialty chemicals, due to its unique chemical structure and properties.
Used in Antioxidant Applications:
2-phenylindazole is used as an antioxidant, providing protection against oxidative stress and damage in various chemical and biological systems, which can be beneficial in the development of new products with enhanced stability and performance.
Used in Antiviral Applications:
As an antiviral agent, 2-phenylindazole is utilized for its potential to inhibit viral replication and infection, offering a promising avenue for the development of new antiviral therapies and treatments.

Upstream product

• 33331-19-0 N-(2-nitrobenzyl)aniline 
• 56222-13-0 N-(2-Phenylaminomethyl-phenyl)-hydroxylamine 
• 32286-81-0 2-phenyl-4,5,6,7-tetrahydro-2H-indazole 
• 17064-77-6 N-(2-nitrobenzylidene)aniline 
• 70704-39-1 3-chloro-2-phenyl-2H-indazole 
• 6319-21-7 2-(hydroxymethyl)azobenzene 
• 10359-18-9 N-(4-nitrobenzyl)aniline 
• 60109-75-3 2-phenylindazoline 
• 262364-62-5 1-o-bromobenzyl-1-phenylhydrazine 
• 1624-50-6 (Ε)-N-(2-nitrobenzylidene)aniline 
• 59-88-1 phenylhydrazine hydrochloride 
• 62-53-3 aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 29483-73-6 2-(2-aminophenyl)benzthiazole 

Downstream Products

• 61063-06-7 7-nitro-2-phenyl-2H-indazole 
• 3682-56-2 2-phenylazo-benzoic acid 
• 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 

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

Microwave enhanced greener synthesis of indazoles via nitrenes

Non-traditional methods (grinding, water-based biphasic reactions, microwave chemistry) were used for the preparation of Schiff bases from several amines and 2-nitrobenzaldehydes. These nitro compounds were allowed to react with triethyl phosphite under m

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.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

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.

Oxidative cross-dehydrogenative coupling (CDC)viaC(sp2)-H bond functionalization:tert-butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2H-indazoles with aldehydes/benzyl alcohols/styrenes

An efficient, cost-effective, transition-metal-free, oxidative C(sp2)-H/C(sp2)-H cross-dehydrogenative couplingviaa C(sp2)-H bond functionalization protocol for the regioselective direct C-3 acylation/benzoylation of subst

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 and cytotoxic activity of combretastatin a-4 and 2,3-diphenyl-2h-indazole hybrids

Cancer is the second leading cause of death, after cardiovascular diseases. Different strategies have been developed to treat cancer; however, chemotherapy with cytotoxic agents is still the most widely used treatment approach. Nevertheless, drug resistance to available chemotherapeutic agents is still a serious problem, and the development of new active compounds remains a constant need. Taking advantage of the molecular hybridization approach, in the present work we designed, synthesized, and tested the cytotoxic activity of two hybrid compounds and seven derivatives based on the structure of combretastatin A-4 and 2,3-diphenyl-2H-indazole. Practical modifications of re-ported synthetic protocols for 2-pheny-2H-indazole and 2,3-dipheny-2H-indazole derivatives under microwave irradiation were implemented. The cytotoxicity assays showed that our designed hybrid compounds possess strong activity, especially compound 5, which resulted even better than the reference drug cisplatin against HeLa and SK-LU-1 cells (IC50 of 0.16 and 6.63 μM, respectively), and it had similar potency to the reference drug imatinib against K562 cells. Additionally, in silico and in vitro studies strongly suggest tubulin as the molecular target for hybrid compound 5.

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.