7731-34-2

Basic information

• Product Name: 2-t-Butyl-3-phenyloxazirane
• Synonyms: 2-t-Butyl-3-phenyloxazirane;alpha-phenyl-N-tert-butyloxaziridine;2-(1,1-Dimethylethyl)-3-phenyloxaziridine;2-tert-Butyl-3-phenyloxaziridine
• CAS NO: 7731-34-2
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Mol File: 7731-34-2.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 224.3°C at 760 mmHg
• Flash Point: 60°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 0.0921mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: 2-t-Butyl-3-phenyloxazirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-t-Butyl-3-phenyloxazirane(7731-34-2)
• EPA Substance Registry System: 2-t-Butyl-3-phenyloxazirane(7731-34-2)

Safety Data

• Hazardous Substances Data: 7731-34-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 6208, 1956 DOI: 10.1021/ja01604a072

InChI:InChI=1/C11H15NO/c1-11(2,3)12-10(13-12)9-7-5-4-6-8-9/h4-8,10H,1-3H3

Upstream product

• 6852-58-0 N-benzylidene tert-butylamine 
• 27151-60-6 1-t-butyl-3-phenylaziridin-2-one 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 529-20-4 2-methylphenyl aldehyde 
• 100-52-7 benzaldehyde 
• 497-19-8 sodium carbonate 
• 75-64-9 tert-butylamine 

Downstream Products

• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 54222-28-5 2,2'-di-tert-butyl-3,3'-diphenyl-4,4'-(4-methyl-m-phenylene)-bis-[1,2,4]oxadiazolidin-5-one 
• 35105-50-1 (2-tert-butyl-3,4-diphenyl-[1,2,4]oxadiazolidin-5-ylidene)-phenyl-amine 
• 54222-26-3 2-tert-butyl-4-(3-isocyanato-4-methyl-phenyl)-3-phenyl-[1,2,4]oxadiazolidin-5-one 
• 69849-46-3 N-tert-butyl-N-(1-phenylpentyl)amine 
• 18150-81-7 N-(diphenylmethyl)-2-methylpropan-2-amine 
• 6852-58-0 N-benzylidene tert-butylamine 
• 106745-24-8 methyl N-tert-butyl-3-phenylisoxazolidine-5-carboxylate 
• 5894-65-5 N-t-butylbenzamide 
• 100-52-7 benzaldehyde 
• 88015-31-0 N-butyl-2-(1-methylethyl)pyrrolidine 
• 88015-33-2 N-butyl-5-methyl-4-hexenamine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 

Relevant articles and documents

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

Synthesis of 4-Isoxazolines via Visible-Light Photoredox-Catalyzed [3 + 2] Cycloaddition of Oxaziridines with Alkynes

A method for [3 + 2] cycloaddition of oxaziridines with alkynes to form 4-isoxazolines via visible-light photoredox catalysis is described. This method is a greener, atom-economical reaction that tolerates various functional groups and provides good to excellent yield. Moreover, the cyclization products can be conveniently converted into tetrasubstituted allylic alcohols and enamines. A mechanistic study suggests that the reaction involves photoredox-catalyzed in situ generation of a nitrone from the oxaziridine by SET.

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.