3400-12-2

Basic information

• Product Name: 2-Methyl-3-phenyloxaziridine
• Synonyms: 2-Methyl-3-phenyloxaziridine;3-propyl-2-methyl-oxaziridine;3-propyl-2-methyl-oxaziridine, 3-Isopropyl-2-methyl-oxaziridine, 3-Ethyl-2,3-dimethyl-oxaziridine
• CAS NO: 3400-12-2
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.1632
• Mol File: 3400-12-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 177.2°Cat760mmHg
• Flash Point: 46.8°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.05mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 2-Methyl-3-phenyloxaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-phenyloxaziridine(3400-12-2)
• EPA Substance Registry System: 2-Methyl-3-phenyloxaziridine(3400-12-2)

Safety Data

• Hazardous Substances Data: 3400-12-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 1628, 1967 DOI: 10.1021/jo01280a080

InChI:InChI=1/C8H9NO/c1-9-8(10-9)7-5-3-2-4-6-7/h2-6,8H,1H3

Upstream product

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

Downstream Products

• 50506-86-0 4-methyl-2-phenyl-5-phenylimino-1,2,4-thidiazolidine-3-thione 
• 50484-08-7 2-benzhydrylidene-3-methyl-5,5-diphenyl-oxazolidin-4-one 
• 88070-48-8 N-methylbenzamide 
• 622-29-7 N-Benzylidenemethylamine 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 65178-52-1 N-allyl-N-methylbenzamide 
• 124687-81-6 [(S)-2-((R)-Benzenesulfinyl)-1-phenyl-ethyl]-methyl-amine 

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.

Action d'un Tetrafluoroborate d'Oxaziridinium sur les Amines et les Imines

The Oxaziridinium salt 1 derived from dihydroisoquinolin is an oxygen transfer reagent to primary amines leading to nitrosoderivatives (if R = Alkyl) or nitro compounds (if R = Aryl), to tertiary amines leading to N-oxides, and to secondary amines and imines leading to the corresponding nitrone.