1357381-89-5

Basic information

• Product Name: 6-nitro-4-phenyl-2H-chromen-2-one
• Synonyms: 6-nitro-4-phenyl-2H-chromen-2-one
• CAS NO: 1357381-89-5
• Molecular Weight: 267.241
• Mol File: 1357381-89-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 6-nitro-4-phenyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-nitro-4-phenyl-2H-chromen-2-one(1357381-89-5)
• EPA Substance Registry System: 6-nitro-4-phenyl-2H-chromen-2-one(1357381-89-5)

Safety Data

• Hazardous Substances Data: 1357381-89-5(Hazardous Substances Data)

Upstream product

• 2725-81-7 6-nitrocoumarin 
• 98-80-6 phenylboronic acid 
• 10242-15-6 6-nitro-2-oxo-2H-chromen-3-carboxylic acid 
• 100-02-7 4-nitro-phenol 
• 830-03-5 4-nitrophenol acetate 
• 103-26-4 methyl cinnamate 
• 153136-77-7 (E)-ethyl 3-(2-hydroxy-5-nitrophenyl)acrylate 
• 373-84-2 difluorotriphenyl-λ⁵-stibane 

Relevant articles and documents

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation

An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient phenolic acetates, affording coumarins with excellent regioselectivity, and proceeds via C-H bond activation proven by deuterium incorporation studies.

A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative Heck reaction

A straightforward and atom-economical base-free palladium-catalyzed regioselective direct arylation of coumarins and chromenones is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows construction of various biologically important flavone and neoflavone backbones.