134920-16-4

Basic information

• Product Name: 2-Oxaziridinecarboxylic acid, 3-phenyl-, methyl ester
• Synonyms: 2-Oxaziridinecarboxylic acid, 3-phenyl-, methyl ester
• CAS NO: 134920-16-4
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Mol File: 134920-16-4.mol

Chemical Properties

• Boiling Point: 234.9±43.0 °C(Predicted)
• Appearance: /
• Density: 1.306±0.06 g/cm3(Predicted)
• PKA: -5.11±0.40(Predicted)
• CAS DataBase Reference: 2-Oxaziridinecarboxylic acid, 3-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxaziridinecarboxylic acid, 3-phenyl-, methyl ester(134920-16-4)
• EPA Substance Registry System: 2-Oxaziridinecarboxylic acid, 3-phenyl-, methyl ester(134920-16-4)

Safety Data

• Hazardous Substances Data: 134920-16-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 27593-61-9 methyl N-phenylmethylenecarbamate 

Downstream Products

• 53842-74-3 methyl L-N-(benzylidene)valil-L-leucinate 
• 134920-19-7 methyl L-N-(methoxycarbonylamino)valyl-L-leucinate 
• 134920-18-6 L-N-(methoxycarbonylamino)valine 
• 135028-04-5 (S)-3-Methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyric acid 
• 24537-42-6 N-(methoxycarbonylamino)cyclohexylamine 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 100-52-7 benzaldehyde 
• 538-51-2 benzylidene phenylamine 
• 2290-03-1 methyl N'-phenylhydrazinoformate 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 199604-72-3 N-methyl 1-hydroxy-1-phenylmethylcarbamate 
• 134920-23-3 L-N-(methoxycarbonylamino)proline 
• 27593-61-9 methyl N-phenylmethylenecarbamate 
• 134920-20-0 N-(methoxycarbonylamino)morpholine 

Relevant articles and documents

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.

Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles

We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).

N-Amination Using N-Methoxycarbonyl-3-phenyloxaziridine. Direct Access to Chiral Nβ-Protected α-Hydrazinoacids and Carbazates

Primary and secondary amines =NH, including α-aminoacids, can be converted under mild conditions to the corresponding carbazates =N-NH-CO2Me, on reaction with N-methoxycarbonyl-3-phenyloxaziridine 1.