63160-13-4

Basic information

• Product Name: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE
• Synonyms: TRANS-2-(PHENYL SULFONYL)-3-PHENYL OXAZIRIDINE;3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE;Oxaziridine, 3-phenyl-2-(phenylsulfonyl;2-(benzenesulfonyl)-3-phenyloxaziridine;trans-2-(Phenylsulfonyl)-3-phenyloxyaziridine;3-Phenyl-N-phenylsulfonyloxaziridine;Davis Oxaziridine;N-(Phenylsulfonyl)phenyloxaziridine
• CAS NO: 63160-13-4
• Molecular Formula: C₁₃H₁₁NO₃S
• Molecular Weight: 261.3
• EINECS: 1533716-785-6
• Product Categories: Aromatics;Heterocycles;Intermediates;Sulfur & Selenium Compounds
• Mol File: 63160-13-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 96-97 °C
• Boiling Point: 394.4 °C at 760 mmHg
• Flash Point: 192.3 °C
• Appearance: /
• Density: 1.398 g/cm³
• Vapor Pressure: 1.99E-06mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: -13.47±0.40(Predicted)
• CAS DataBase Reference: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(63160-13-4)
• EPA Substance Registry System: 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE(63160-13-4)

Safety Data

• Hazardous Substances Data: 63160-13-4(Hazardous Substances Data)

Usage

Description

3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine, also known as Davis Oxaziridine, is an organic compound with the molecular formula C15H13NO2S. It is a derivative of oxaziridine, which is a heterocyclic compound containing an oxygen and a nitrogen atom. 3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE is characterized by its oxidizing properties, making it a valuable reagent in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is used as an oxidizing agent for the preparation of a wide variety of pharmaceutical compounds. Its ability to selectively oxidize various functional groups, such as alcohols and amines, makes it a versatile and valuable tool in the synthesis of complex molecules, including those with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is employed as a reagent for the oxidation of various substrates, including alcohols, amines, and sulfides. Its selective oxidation properties allow chemists to introduce new functional groups into molecules, enabling the synthesis of a diverse range of compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine is also utilized in research and development settings, where it serves as a key reagent for the synthesis of novel compounds and the investigation of new reaction mechanisms. Its unique properties and reactivity make it an essential tool for chemists working on the design and synthesis of new molecules with potential applications in various fields.

InChI:InChI=1/C13H11NO3S/c15-18(16,12-9-5-2-6-10-12)14-13(17-14)11-7-3-1-4-8-11/h1-10,13H

Synthetic route

(S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one (959937-89-4) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Stage #1: (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78 - -40℃; for 0.75h; Stage #2: With N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran at -78℃; for 2h;
Stage #1: (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one With sodium hexamethyldisilazane In tetrahydrofuran at -78 - -40℃; for 0.75h; Stage #2: With N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran at -78℃; for 2h;

3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid (959937-90-7) → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: triethylamine / diethyl ether; dichloromethane / 1.08 h / -78 - 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 3 h / -78 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 3.2: 2 h / -78 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / diethyl ether; dichloromethane / 1.08 h / -78 - 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 2.2: 3 h / -78 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 3.2: 2 h / -78 °C View Scheme

C28H37NO7S → (S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 3 h / -78 - 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 2.2: 2 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C 1.2: 3 h / -78 - 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 - -40 °C 2.2: 2 h / -78 °C View Scheme

(S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4) + trimethoxonium tetrafluoroborate (420-37-1) → (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (1005478-61-4)

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 0 - 20℃; for 3h; Molecular sieve;

(S)-4-benzyl-3-{(S)-2-hydroxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (63160-13-4) → (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one (1005478-61-4)

Conditions	Yield
With trimethoxonium tetrafluoroborate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 0 - 20℃; Molecular sieve;

Upstream product

• 959937-90-7 3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionic acid 
• 959937-89-4 (S)-4-benzyl-3-{3-[(2S,5R)-5-(4-methoxybenzyloxy)-1-(toluene-4-sulphonyl)piperidin-2-yl]propionyl}oxazolidin-2-one 
• 13909-34-7 N-benzylidenephenylsulfonamide 

Downstream Products

• 1005478-61-4 (S)-4-benzyl-3-{(S)-2-methoxy-3-[(2S,5R)-5-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propionyl}-oxazolidin-2-one 

Relevant articles and documents

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

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