199604-16-5

Basic information

• Product Name: Carbamic acid, N-[(4-methylphenyl)methylene]-, methyl ester
• Synonyms: Carbamic acid, N-[(4-methylphenyl)methylene]-, methyl ester
• CAS NO: 199604-16-5
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 199604-16-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, N-[(4-methylphenyl)methylene]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, N-[(4-methylphenyl)methylene]-, methyl ester(199604-16-5)
• EPA Substance Registry System: Carbamic acid, N-[(4-methylphenyl)methylene]-, methyl ester(199604-16-5)

Safety Data

• Hazardous Substances Data: 199604-16-5(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 1291088-05-5 methyl 3-(benzyloxycarbonylamino)-2,2-diphenyl-3-p-tolylpropanoate 

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.