4535-09-5

Basic information

• Product Name: N-9H-fluoren-9-ylidene-N-phenylamine oxide
• CAS NO: 4535-09-5
• Molecular Formula: C₁₉H₁₃NO
• Molecular Weight: 271.3126
• Mol File: 4535-09-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 503.3°C at 760 mmHg
• Flash Point: 248.1°C
• Density: 1.254g/cm³
• Vapor Pressure: 9.23E-10mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: N-9H-fluoren-9-ylidene-N-phenylamine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: N-9H-fluoren-9-ylidene-N-phenylamine oxide(4535-09-5)
• EPA Substance Registry System: N-9H-fluoren-9-ylidene-N-phenylamine oxide(4535-09-5)

Safety Data

• Hazardous Substances Data: 4535-09-5(Hazardous Substances Data)

Upstream product

• 65478-48-0 S-(9-Fluorenyl)-N-methylisothioharnstoff 
• 586-96-9 Nitrosobenzene 
• 1940-57-4 9H-fluoren-9-yl bromide 
• 486-25-9 9-fluorenone 
• 2157-52-0 9-fluorenone oxime 
• 62-53-3 aniline 
• 20204-22-2 (9-fluorenyl)dimethylsulfonium bromide 
• 13629-22-6 fluoren-9-ylidene-hydrazine 
• 201024-81-9 C,N-diphenylnitrone 
• 71-43-2 benzene 
• 832-80-4 9-diazofluorenone 
• 19126-15-9 9-methoxyfluorene 
• 98-95-3 nitrobenzene 
• 72393-25-0 fluoren-9-yl-dimethyl sulfonium-betaine 

Relevant articles and documents

Single-Step Approach toward Nitrones via Pyridinium Ylides: The DMAP-Catalyzed Reaction of Benzyl Halides with Nitrosoarenes

A single-step approach is reported for the preparation of nitrones from benzyl halides and nitrosoarenes via pyridinium ylides, utilizing 4-dimethylaminopyridine (DMAP) catalyst and mild reaction conditions (Li2CO3, dimethylacetamide, and room temperature). The reaction provides both keto-and aldonitrones in high yields with a wide scope for benzyl halides and nitrosoarenes. In the same reaction system, 2-methyl-2-nitrosopropane, which does not have an aryl group, also affords the corresponding N-tert-butyl nitrones from primary benzyl bromides that have an electron-withdrawing group. As an application of the reaction, methyl 2-bromo-2-phenylacetate was used to prepare the corresponding isoxazolidine by a sequential one-pot synthesis.

A Protocol to Transform Sulfones into Nitrones and Aldehydes

A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.

Cycloaddition of Fluorenone N-Aryl Nitrones with Methylenecyclopropanes and Sequential 1,3-Rearrangement: An Entry to Synthesis of Spirofluorenylpiperidin-4-ones

A facile synthesis of various spirofluorenylpiperidin-4-ones has been achieved in good yields from fluorenone N-aryl nitrones and methylenecyclopropanes. This method involved an initial cycloaddition to form a 5-spirocyclopropane-isoxazoline, which underwent a highly selective 1,3-rearrangement to give the desired product. The stereochemistry of the spirofluorenylpiperidin-4-one could be controlled by the cycloaddition and sequential rearrangement strategy. Furthermore, the spirofluorenylpiperidin-4-ones could be not only prepared in one-pot procedure but also converted to useful scaffolds by reduction or oxidation conditions.