120455-03-0

Basic information

• Product Name: 5-METHOXY-2-PHENYL-2H-INDAZOLE
• Synonyms: 5-METHOXY-2-PHENYL-2H-INDAZOLE
• CAS NO: 120455-03-0
• Molecular Formula: C₁₄H₁₂N₂O
• Molecular Weight: 224.25788
• Mol File: 120455-03-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHOXY-2-PHENYL-2H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-2-PHENYL-2H-INDAZOLE(120455-03-0)
• EPA Substance Registry System: 5-METHOXY-2-PHENYL-2H-INDAZOLE(120455-03-0)

Safety Data

• Hazardous Substances Data: 120455-03-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 21650-49-7 (E)-1-(4-methoxyphenyl)-2-phenyldiazene 
• 262364-69-2 N-(2-bromo-5-methoxy-benzyl)-N-phenyl-hydrazine 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 326-04-5 N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide 
• 100-63-0 phenylhydrazine 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 95547-09-4 CH₃OC₆H₃(CHNC₆H₅)Br 
• 17637-72-8 N-(3-methoxybenzylidene)aniline 
• 591-31-1 3-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 6415-68-5 N-nitroso-N-phenylglycine 

Relevant articles and documents

Heterogeneous Photocatalytic Reactions of Azobenzenes on Titanium Dioxide Powder in Methanolic Solution

Irradiation of a TiO2 powder suspension in a methanolic solution of an azobenzene results in the formation of 1,2,4-triphenyl-1,2,4-triazolidines and a 2-phenylindazole in moderate 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.

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

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.

Synthesis method of 2H-indazole and derivatives thereof

The invention discloses a synthetic reaction of 2H-indazole and derivatives thereof under a metal-free condition. The new strategy has the advantages of no metal participation, wide substrate range and good functional group compatibility, and an efficient

Efficient synthesis of 2-aryl-2: H -indazoles by base-catalyzed benzyl C-H deprotonation and cyclization

A straightforward and efficient method for the preparation of 2-aryl-2H-indazoles from ortho-alkyl substituted azoxybenzenes is presented. The reaction proceeds through base-catalyzed benzyl C-H deprotonation and cyclization to afford 2-aryl-2H-indazoles

Regioselective synthesis of 2 H-indazoles using a mild, one-pot condensation-cadogan reductive cyclization

An operationally simple and efficient one-pot synthesis of 2H-indazoles from commercially available reagents is reported. Ortho-imino-nitrobenzene substrates, generated via condensation, undergo reductive cyclization promoted by tri-n-butylphosophine to afford substituted 2H-indazoles under mild reaction conditions. A variety of electronically diverse ortho-nitrobenzaldehydes and anilines were examined. To further extend the scope of the transformation, aliphatic amines were also employed to form N2-alkyl indazoles selectively under the optimized reaction conditions.

Mesoporous nitrogen doped nano titania - A green photocatalyst for the effective reductive cleavage of azoxybenzenes to amines or 2-phenyl indazoles in methanol

A new nitrogen precursor, hydrazine hydrate was used in the synthesis of nano-sized, N-doped TiO2 photocatalyst by a simple wet impregnation method. This photocatalyst was characterized by X-ray diffraction (XRD), Brunauer-Emmett-Teller (BET), High resolution transmission electron microscope (HR-TEM), UV-vis diffuses reflectance spectra (DRS), photoluminescence (PL) and X-ray photoelectron spectroscopy (XPS). XRD patterns show that the crystal structure of N-TiO2 resembles anatase phase of TiO2. The UV-vis spectra indicate an increase in absorption of visible light when compared to TiO2. Furthermore XPS analysis reveals the presence of the N atom as O-Ti-N linkage substituting the O atom in the TiO2 lattice and this causes a decrease in oxygen vacancies. N-TiO2 nanoparticles were used as a green and recyclable heterogeneous photocatalyst for rapid and efficient reductive cleavage of azoxybenzene into their corresponding amines or 2-phenylindazoles with methanol at room temperature under N2 atmosphere. Azoxybenzenes in neat methanol afforded anilines, while in aqueous methanol (20% water-80% methanol) they formed corresponding 2-phenyl indazoles. In both reductive cleavages, nano N-TiO2 is more effective than prepared TiO2, showing that the nitrogen doping could be an excellent choice to improve the photoactivity of TiO2.

Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl

Synthesis of 2-aryl-2H-indazoles via copper(I)-catalyzed intramolecular amination reaction

A versatile method for the preparation of 2-aryl-2H-indazoles was developed by copper(I)-catalyzed intramolecular amination reaction under the conditions of [CuI/Cs2CO3(250 mol%)/1,4-dioxane/105°C] starting from N'-aryl-N'-(o-bromobe