21236-85-1

Basic information

• Product Name: quinoline-4-carbonitrile 1-oxide
• Synonyms: 4-Cyanoquinoline 1-oxide; 4-Quinolinecarbonitrile 1-oxide; 4-Quinolinecarbonitrile, 1-oxide
• CAS NO: 21236-85-1
• Molecular Formula: C₁₀H₆N₂O
• Molecular Weight: 170.1674
• Mol File: 21236-85-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 389.2°C at 760 mmHg
• Flash Point: 189.2°C
• Density: 1.2g/cm³
• Vapor Pressure: 2.9E-06mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: quinoline-4-carbonitrile 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: quinoline-4-carbonitrile 1-oxide(21236-85-1)
• EPA Substance Registry System: quinoline-4-carbonitrile 1-oxide(21236-85-1)

Safety Data

• Hazardous Substances Data: 21236-85-1(Hazardous Substances Data)

Upstream product

• 2973-27-5 quinoline-4-carbonitrile 
• 2508-86-3 4-aminoquinoline 1-oxide 

Downstream Products

• 100517-53-1 3-hydroxy-quinoline-4-carbonitrile 
• 63158-99-6 2-oxo-1,2-dihydro-quinoline-4-carbonitrile 
• 63158-99-6 2-hydroxy-quinoline-4-carbonitrile 
• 2973-26-4 2-phenyl-4-quinolinecarbonitrile 
• 29312-45-6 1-oxy-2-phenyl-quinoline-4-carbonitrile 
• 74831-35-9 C₂₂H₁₅N₂O 
• 74831-37-1 1-Hydroxy-2,2-diphenyl-1,2-dihydro-quinoline-4-carbonitrile 
• 118-13-8 3-hydroxyquinoline-4-carboxylic acid 
• 379722-76-6 2-methoxy-4-cyanoquinoline 1-oxide 

Relevant articles and documents

From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.

Dehydrogenative etherification homocoupling of heterocyclic N-oxides

A novel approach was developed for the dehydrogenative etherification homocoupling of heterocyclic N-oxides in the presence of silver oxide and PyBroP. Various substrates were well tolerated and the desired products were obtained in moderate to good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and good regioselectivity.