126527-21-7

Basic information

• Product Name: (E)-picolinaldehyde O-benzyl oxime
• Synonyms: (E)-picolinaldehyde O-benzyl oxime
• CAS NO: 126527-21-7
• Molecular Weight: 212.251
• Mol File: 126527-21-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-picolinaldehyde O-benzyl oxime(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-picolinaldehyde O-benzyl oxime(126527-21-7)
• EPA Substance Registry System: (E)-picolinaldehyde O-benzyl oxime(126527-21-7)

Safety Data

• Hazardous Substances Data: 126527-21-7(Hazardous Substances Data)

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 1193-96-0 (E)-pyridin-2-aldoxime 
• 100-44-7 benzyl chloride 

Downstream Products

• 1006365-28-1 O-benzyl-N-(1-(pyridin-2-yl)but-3-enyl)hydroxylamine 

Relevant articles and documents

Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry

The kinetic and thermodynamic selectivities of imine formation have been investigated for several dynamic covalent libraries of aldehydes and amines. Two systems were examined, involving the reaction of different types of primary amino groups (aliphatic amines, alkoxy-amines, hydrazides and hydrazines) with two types of aldehydes, sulfobenzaldehyde and pyridoxal phosphate in aqueous solution at different pD (5.0, 8.5, 11.4) on one hand, 2-pyridinecarboxaldehyde and salicylaldehyde in organic solvents on the other hand. The reactions were performed separately for given amine/aldehyde pairs as well as in competitive conditions between an aldehyde and a mixture of amines. In the latter case, the time evolution of the dynamic covalent libraries generated was followed, taking into consideration the operation of both kinetic and thermodynamic selectivities. The results showed that, in aqueous solution, the imine of the aliphatic amine was not stable, but oxime and hydrazone formed well in a pH dependent way. On the other hand, in organic solvents, the kinetic product was the imine derived from an aliphatic amine and the thermodynamic products were oxime and hydrazone. The insights gained from these experiments provide a basis for the implementation of imine formation in selective derivatization of mono-amines in mixtures as well as of polyfunctional compounds presenting different types of amino groups. They may in principle be extended to other dynamic covalent chemistry systems.

A metathesis-based approach to the synthesis of 2-pyridones and pyridines

(Chemical Equation Presented) The ring-closing metathesis reaction has been successfully employed to form a range of dihydropyridone intermediates, which are in the correct oxidation state to undergo a base-induced elimination to reveal the aromatic 2-pyridone. This mild and novel approach to six-membered heteroaromatic compounds then provides access to a wide variety of substituted pyridines in excellent overall yield.