385446-23-1

Basic information

• Product Name: N-(4-(benzyloxy)phenyl)-1-phenylmethanimine
• Synonyms: N-(4-(benzyloxy)phenyl)-1-phenylmethanimine
• CAS NO: 385446-23-1
• Molecular Weight: 287.361
• Mol File: 385446-23-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(4-(benzyloxy)phenyl)-1-phenylmethanimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-(benzyloxy)phenyl)-1-phenylmethanimine(385446-23-1)
• EPA Substance Registry System: N-(4-(benzyloxy)phenyl)-1-phenylmethanimine(385446-23-1)

Safety Data

• Hazardous Substances Data: 385446-23-1(Hazardous Substances Data)

Upstream product

• 1145-76-2 benzyl 4-nitrophenyl ether 
• 100-51-6 benzyl alcohol 
• 6373-46-2 p-benzyloxyaniline 
• 94040-95-6 1-azido-4-(benzyloxy)benzene 
• 6554-98-9 trans-4-Hydroxystilbene 
• 100-52-7 benzaldehyde 

Downstream Products

• 39860-72-5 N-benzyl-4-(benzyloxy)aniline 
• 1221717-79-8 C₂₆H₂₇NO₃ 

Relevant articles and documents

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.