73844-99-2

Basic information

• Product Name: 2-(methylsulfonyl)-3-phenyloxaziridine
• CAS NO: 73844-99-2
• Molecular Formula: C₈H₉NO₃S
• Molecular Weight: 199.227
• Mol File: 73844-99-2.mol

Chemical Properties

• Boiling Point: 300.8°C at 760 mmHg
• Flash Point: 135.7°C
• Density: 1.44g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 2-(methylsulfonyl)-3-phenyloxaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(methylsulfonyl)-3-phenyloxaziridine(73844-99-2)
• EPA Substance Registry System: 2-(methylsulfonyl)-3-phenyloxaziridine(73844-99-2)

Safety Data

• Hazardous Substances Data: 73844-99-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(methylsulfonyl)-3-phenyloxaziridine is used as a synthetic intermediate for its reactivity as a powerful oxygen transfer agent. This makes it a valuable compound in the synthesis of various organic molecules.
Used in Oxygen Transfer Reactions:
2-(methylsulfonyl)-3-phenyloxaziridine is used as a reagent in oxygen transfer reactions, where it can efficiently transfer oxygen to other molecules, facilitating the formation of new compounds.
Used in Asymmetric Oxidation of Sulfides:
2-(methylsulfonyl)-3-phenyloxaziridine is used as a reagent for the asymmetric oxidation of sulfides, a reaction that is important in the synthesis of chiral compounds, which are essential in the pharmaceutical industry.
Used in Pharmaceutical Research:
2-(methylsulfonyl)-3-phenyloxaziridine is used as a compound of interest in pharmaceutical research due to its potential antitumor and cytotoxic properties. Its study may lead to the development of new drugs for cancer treatment.

Upstream product

• 73845-05-3 N-methanesulfonyl benzylideneamine 
• 774-48-1 (diethoxymethyl)benzene 
• 73845-05-3 (E)-N-benzylidenemethanesulfonamide 

Relevant articles and documents

X-Ray Structure and Stereochemical Properties of (S,S)-(-)-2-Methylsulphonyl-3-phenyloxaziridine and of (S,S)-(-)-2-Methylsulphonyl-3-(2-chloro-5-nitrophenyl)oxaziridine

X-Ray analysis of crystalline, optically pure 2-methylsulphonyl-3-phenyloxaziridine (2a) and 2-methylsulphonyl-3-(2-chloro-5-nitrophenyl)oxaziridine (2b), obtained by asymmetric oxidation of the corresponding prochiral N-benzylidenemethylsulphonylimine (1

ASYMMETRIC SYNTHESIS AND STEREOCHEMICAL PROPERTIES OF OPTICALLY ACTIVE N-SULPHONYL-3-ARYLOXAZIRIDINES

Oxidation of prochiral sulphonimines (RSO2N = CHAr) with (1S)-(+)-PCA, followed by fractional crystallization of the crude reaction products, provides highly optically-pure N-sulphonyl-3-aryloxaziridines 1H-NMR spectra recorded in the presence of chiral solvent or shift reagent, CD spectra, and the results observed by using them as new chiral oxidizing reagents, are also reported.

Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines

A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.