39245-63-1

Basic information

• Product Name: Oxaziridine, 2-methyl-3-phenyl-, (2R,3S)-rel-
• CAS NO: 39245-63-1
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Mol File: 39245-63-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Oxaziridine, 2-methyl-3-phenyl-, (2R,3S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxaziridine, 2-methyl-3-phenyl-, (2R,3S)-rel-(39245-63-1)
• EPA Substance Registry System: Oxaziridine, 2-methyl-3-phenyl-, (2R,3S)-rel-(39245-63-1)

Safety Data

• Hazardous Substances Data: 39245-63-1(Hazardous Substances Data)

Upstream product

• 622-29-7 N-Benzylidenemethylamine 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 73311-38-3 C₂₀H₁₅NO 
• 70766-02-8 N-(9H-fluoren-9-ylidene)-1-phenylmethanamine 
• 16118-22-2 benzylidenamine 

Downstream Products

• 124687-81-6 [(S)-2-((R)-Benzenesulfinyl)-1-phenyl-ethyl]-methyl-amine 
• 65178-52-1 N-allyl-N-methylbenzamide 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 74-85-1 ethene 
• 13849-02-0 N,N'-bis(methyl)sulphur di-imide 
• 100-52-7 benzaldehyde 
• 877-80-5 N-methyl-4-nitrobenzylideneamine 
• 88070-48-8 N-methylbenzamide 
• 622-29-7 N-Benzylidenemethylamine 
• 4143-42-4 (Z)-azomethane 
• 110-83-8 cyclohexene 
• 50484-08-7 2-benzhydrylidene-3-methyl-5,5-diphenyl-oxazolidin-4-one 
• 50506-86-0 4-methyl-2-phenyl-5-phenylimino-1,2,4-thidiazolidine-3-thione 

Relevant articles and documents

Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights

A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.

[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants

Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.

Simple and highly efficient synthesis of oxaziridines by tetrabutylammonium Oxone

Oxygenation of various aldimines with tetrabutylammonium monoperoxysulfate produced the corresponding E- or a mixture of E- and Z-oxaziridines with very high yields (≥90%) and good to excellent selectivities (75-100%) within 20min to 10h in CH3CN at room temperature (～25°C). The E/Z isomer ratio critically depends on the stereo-electronic nature of the substituents in the oxaziridines, solvent, and the presence of Lewis acids and bases.