440096-20-8

Basic information

• Product Name: 4,5,6,7-TETRAFLUORO-3-PHENYL-1H-INDAZOLE
• Synonyms: 4,5,6,7-TETRAFLUORO-3-PHENYL-1H-INDAZOLE
• CAS NO: 440096-20-8
• Molecular Formula: C₁₃H₆F₄N₂
• Molecular Weight: 266.1937528
• Mol File: 440096-20-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,5,6,7-TETRAFLUORO-3-PHENYL-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-TETRAFLUORO-3-PHENYL-1H-INDAZOLE(440096-20-8)
• EPA Substance Registry System: 4,5,6,7-TETRAFLUORO-3-PHENYL-1H-INDAZOLE(440096-20-8)

Safety Data

• Hazardous Substances Data: 440096-20-8(Hazardous Substances Data)

Upstream product

• 1536-23-8 2,3,4,5,6-pentafluorobenzophenone 
• 93-58-3 benzoic acid methyl ester 
• 344-04-7 bromopentafluorobenzene 

Downstream Products

• 1378981-72-6 [K(F₁₂-Tp^4Bo,3Ph)] 
• 1360075-80-4 [Tl(F₁₂-Tp^4Bo,3Ph)] 

Relevant articles and documents

C-H activation dependent Pd-catalyzed carbonylative coupling of (hetero)aryl bromides and polyfluoroarenes

The carbonylative coupling of aryl and heteroaryl bromides with polyfluoroarenes via palladium-catalyzed C-H activation is presented. This transformation proceeds efficiently at moderate reaction temperatures and does not require strong base or reactive intermediates. A near stoichiometric amount of CO is sufficient and the methodology can thus be easily expanded to include the preparation of [13C]-acyl labeled benzopolyfluorophenones.

Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation

In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors.