10437-90-8

Basic information

• Product Name: 3-phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene
• Synonyms: 3-phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene
• CAS NO: 10437-90-8
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.23772
• Mol File: 10437-90-8.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(10437-90-8)
• EPA Substance Registry System: 3-phenyl-2-oxa-3-azabicyclo[2.2.2]oct-5-ene(10437-90-8)

Safety Data

• Hazardous Substances Data: 10437-90-8(Hazardous Substances Data)

Upstream product

• 60-29-7 diethyl ether 
• 1165952-91-9 cyclohexa-1,3-diene 
• 586-96-9 Nitrosobenzene 
• 64-17-5 ethanol 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 

Downstream Products

• 68234-27-5 1′,2′,3′,6′-tetrahydro-[1,1′-biphenyl]-2-amine 

Relevant articles and documents

Super electron donor-mediated reductive transformation of nitrobenzenes: A novel strategy to synthesize azobenzenes and phenazines

The transformation of nitrobenzenes into azobenzenes by pyridine-derived super electron donor 2 is described. This method provides an efficient synthesis of azobenzenes because of not requiring the use of expensive transition-metals, toxic or flammable reagents, or harsh conditions. Moreover, when using 2-fluoronitrobenzenes as substrates, phenazines were found to be obtained. The process affords a novel synthesis of phenazines.

Titania-Supported Gold Nanoparticles Catalyze the Selective Oxidation of Amines into Nitroso Compounds in the Presence of Hydrogen Peroxide

In this article, the catalytic activity of titania-supported gold nanoparticles (Au/TiO2) was studied for the selective oxidation of amines into nitroso compounds using hydrogen peroxide (H2O2). Gold nanoparticles deposited on Degussa P25 polymorphs of titania (TiO2) have been found to promote the selective formation of a variety of nitroso arenes in high yields and selectivities, even in a large-scale synthesis. In contrast, alkyl amines are oxidized to the corresponding oximes under the examined conditions. Kinetic studies indicated that aryl amines substituted with electron-donating groups are oxidized faster than the corresponding amines bearing an electron-withdrawing functionality. A Hammett-type kinetic analysis of a range of para-X-substituted aryl amines implicates an electron transfer (ET) mechanism (ρ=-1.15) for oxidation reactions with concomitant formation of the corresponding N-aryl hydroxylamine as possible intermediate. We also show that the oxidation protocol of aryl amines in the presence of 1,3-cyclohexadiene leads in excellent yields to the corresponding hetero Diels-Alder adducts between the diene and the in situ formed nitrosoarenes.

X-ray structural analysis for the prediction on the nature of the retro DielsAlder pathway: Concerted or stepwise. structural studies on nitrosobenzene cycloadducts

Crystal structures of nitrosobenzene cycloadducts 57 reveal structural effects consistent with the early stages of the retro DielsAlder fragmentation. There is a clear differentiation between the structure parameters of cycloadduct 5, which reacts by a co