163226-26-4

Basic information

• Product Name: tert-butyl 2,4-dichlorobenzylidenecarbamate
• Synonyms: tert-butyl 2,4-dichlorobenzylidenecarbamate
• CAS NO: 163226-26-4
• Molecular Weight: 274.147
• Mol File: 163226-26-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl 2,4-dichlorobenzylidenecarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2,4-dichlorobenzylidenecarbamate(163226-26-4)
• EPA Substance Registry System: tert-butyl 2,4-dichlorobenzylidenecarbamate(163226-26-4)

Safety Data

• Hazardous Substances Data: 163226-26-4(Hazardous Substances Data)

Upstream product

• 1415728-57-2 tetr-butyl ((2,4-dichlorophenyl)(phenylsulfonyl)methyl)carbamate 
• 150884-56-3 N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine 
• 150884-51-8 1,1-dimethylethyl N-[(4-cyanophenyl)methylen]carbamate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 68014-21-1 triphenyl(t-butoxycarbonylimino)phosphorane 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 1415114-05-4 (R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-amine 
• 1246770-52-4 ((R)-N-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide) 
• 1415728-54-9 (R)-tert-butyl (2-amino-1-(2,4-dichlorophenyl)ethyl)carbamate 
• 1415728-60-7 (R)-tert-butyl (1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl)carbamate 
• 1415728-55-0 (R)-tert-butyl (1-(2,4-dichlorophenyl)-2-nitroethyl)carbamate 
• 163226-30-0 N-tert-butoxycarbonyl-3-(2,4-dichlorophenyl)oxaziridine 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Relevant articles and documents

Direct Catalytic Asymmetric Mannich-Type Reaction en Route to α-Hydroxy-β-amino Acid Derivatives

A direct catalytic Mannich-type reaction of α-oxygen-functionalized amides was achieved. The use of 7-azaindoline amide was crucial to facilitate direct enolization and subsequent stereoselective addition to imines in a cooperative catalytic system comprising a soft Lewis acid and Br?nsted base. The operationally simple room-temperature protocol furnished a syn-Mannich adduct with high stereoselectivity. Divergent functional group transformation of the amide moiety of the product allowed for expeditious access to enantioenriched syn-configured α-hydroxy-β-amino carboxylic acid derivatives, highlighting the synthetic utility of the present catalysis.

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.