38636-02-1

Basic information

• Product Name: N-benzyl-O-benzoylhydroxylamine
• Synonyms: N-benzyl-O-benzoylhydroxylamine
• CAS NO: 38636-02-1
• Molecular Weight: 227.263
• Mol File: 38636-02-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: N-benzyl-O-benzoylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-O-benzoylhydroxylamine(38636-02-1)
• EPA Substance Registry System: N-benzyl-O-benzoylhydroxylamine(38636-02-1)

Safety Data

• Hazardous Substances Data: 38636-02-1(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 94-36-0 dibenzoyl peroxide 
• 60-29-7 diethyl ether 
• 3376-26-9 N-Benzylidenebenzylamine N-oxide 
• 7732-18-5 water 
• 98-88-4 benzoyl chloride 
• 24850-33-7 allyltributylstanane 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 65-85-0 benzoic acid 

Downstream Products

• 622-30-0 N-benzyl hydroxylalmine 
• 65-85-0 benzoic acid 
• 19264-38-1 N-benzyldibenzamide 
• 1485-70-7 N-benzylbenzamide 
• 1500-35-2 1-benzyl-1-hydroxy-3-phenyl-urea 
• 1500-26-1 2-benzyl-4-phenyl-[1,2,4]oxadiazolidine-3,5-dione 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Catalytic asymmetric diaziridination

The first catalytic enantio- and diastereoselective synthesis of diaziridines is presented. Aziridination of N-tosyl aldimines applying modified hydroxylamine under asymmetric phase-transfer catalysis furnished optically active diaziridines. The diaziridines are formed as a single diastereomer in up to 96% ee, containing two orthogonal N-protecting groups, which can be deprotected selectively.

Direct N-O bond formation via oxidation of amines with benzoyl peroxide

Herein, we report a general and efficient method for direct N-O bond formation without undesirable C-N bond (amide) formation starting from commercially available amines and benzoyl peroxide. The oxidation of 1,2-diamines to furnish bis-(benzoyloxy)-1,2-diamines is reported for the first time. We found that a significant amount of water (BPO?:?water = 3?:?1) in combination with Cs2CO3 is necessary to achieve high selectivity and yield. The reaction conditions are applicable to a wide range of 1,2-diamine and 1,2-disubstituted-1,2-diamine substrates. Additionally this method is highly applicable to primary and secondary amines. Further, the present method can access chiral bis-hydroxamic acids and bis-hydroxyl amines in just two steps from 1,2-diamines. The reaction conditions are simple, mild and inert atmosphere free. The synthetic potential of this methodology is further demonstrated in the short synthesis of a chiral BHA ligand.

Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes

A variety of primary amines (R-NH2) were converted to their corresponding N-(benzoyloxy)amines (i.e., R-NHOCOPh) under biphasic conditions in excellent yields (63-90%). The intermediate N- (benzoyloxy)amines were converted to their N-ethylamine derivatives upon reaction with triethylborane in THF in good yield (54-89%). These experiments demonstrated the similar chemistry of N-chloro- and N-(benzoyloxy)amines with organoboranes.