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 
• 103-01-5 N-Phenylglycine 
• 508191-77-3 3-phenylsydnone 
• 556812-41-0 4-methoxy-2-(trimethylsilyl)phenyl triflate 
• 6415-68-5 N-nitroso-N-phenylglycine 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 326-04-5 N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 62-53-3 aniline 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 100-63-0 phenylhydrazine 
• 591-31-1 3-methoxy-benzaldehyde 
• 17637-72-8 N-(3-methoxybenzylidene)aniline 

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.

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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.

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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.

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