91002-55-0

Basic information

• Product Name: 2H-Indazole, 3-bromo-2-phenyl-
• CAS NO: 91002-55-0
• Molecular Formula: C13H9BrN2
• Molecular Weight: 273.132
• Mol File: 91002-55-0.mol

Chemical Properties

• CAS DataBase Reference: 2H-Indazole, 3-bromo-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indazole, 3-bromo-2-phenyl-(91002-55-0)
• EPA Substance Registry System: 2H-Indazole, 3-bromo-2-phenyl-(91002-55-0)

Safety Data

• Hazardous Substances Data: 91002-55-0(Hazardous Substances Data)

Upstream product

• 3682-71-1 2-phenyl-2H-indazole 
• 62-53-3 aniline 
• 17064-77-6 N-(2-nitrobenzylidene)aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 586-96-9 Nitrosobenzene 

Downstream Products

• 91002-56-1 3,5-Dibromo-2-phenyl-2H-indazole 
• 91002-57-2 3,7-Dibromo-2-phenyl-2H-indazole 
• 91002-58-3 3,5,7-Tribromo-2-phenyl-2H-indazole 

Relevant articles and documents

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.

Room-Temperature, Metal-Free, and One-Pot Preparation of 2H-Indazoles through a Mills Reaction and Cyclization Sequence

The Mills reaction and cyclization of readily available 2-aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2H-indazoles in up to 88 % yields. In the metal-free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2H-indazole could also be obtained through the one-pot sequence.