90289-56-8

Basic information

• Product Name: 1H-Indole, 3-[(1E)-2-isocyanoethenyl]-
• CAS NO: 90289-56-8
• Molecular Formula: C11H8N2
• Mol File: 90289-56-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-[(1E)-2-isocyanoethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-[(1E)-2-isocyanoethenyl]-(90289-56-8)
• EPA Substance Registry System: 1H-Indole, 3-[(1E)-2-isocyanoethenyl]-(90289-56-8)

Safety Data

• Hazardous Substances Data: 90289-56-8(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 41003-94-5 diethyl isocyanomethylphosphonate 
• 99128-10-6 (isocyanomethyl)triphenylphosphonium chloride 

Relevant articles and documents

Synthesis of Vinyl Isocyanides and Development of a Convertible Isonitrile

The reaction of isocyanomethylenetriphenylphosphorane, generated in situ from the corresponding phosphonium salt, with a diverse set of aldehydes afforded vinyl isocyanides in good to high yields. Excellent E-selectivity was observed for aliphatic aldehydes and 2,6-disubstituted aromatic aldehydes, whereas Z-olefins were formed predominantly with ortho-substituted aryl aldehydes. (Z)-1-Bromo-2-(2-isocyanovinyl)benzene (5l) was found to be a truly universal isonitrile since, after Ugi reaction, the resulting secondary amide unit (RNHCO-) is convertible under both acidic and basic conditions. The application of 5l in the synthesis of polyheterocycles is also illustrated.