53645-44-6

Basic information

• Product Name: 3ξ-indol-3-yl-2-phenyl-acrylonitrile
• Synonyms: 3ξ-indol-3-yl-2-phenyl-acrylonitrile
• CAS NO: 53645-44-6
• Molecular Weight: 244.296
• Mol File: 53645-44-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3ξ-indol-3-yl-2-phenyl-acrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3ξ-indol-3-yl-2-phenyl-acrylonitrile(53645-44-6)
• EPA Substance Registry System: 3ξ-indol-3-yl-2-phenyl-acrylonitrile(53645-44-6)

Safety Data

• Hazardous Substances Data: 53645-44-6(Hazardous Substances Data)

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 140-29-4 phenylacetonitrile 
• 75629-45-7 (Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole 

Relevant articles and documents

PREPARATION AND REACTIONS OF 3-(AMINOMETHYLENE)-3H-INDOLES

A series of 3-(aminomethylene)-3H-indoles (1a-e and 6a-8a) was prepared by the condensation of 3-indolecarbaldehydes (2-5) with secondary amines.Among them, 3-(1-pyrrolidinylmethylene)-3H-indoles (1a and 6a-8a) were obtained as stable colorless prisms, while 3-(piperidinomethylene)-3H-indole (1b) and 3-(morpholinomethylene)-3H-indole (1c) readily polymerized in refluxing benzene.Reaction of 1 with electrophiles, such as alkyl and acyl halides, gave 1-substituted 3-aminomethylene-3H-indolium salts, which were converted to the corresponding 1-substituted 3-indolecarbaldehydes by hydrolysis.Reaction of 1 with active methylene compounds proceeded under mild reaction conditions to afford the corresponding condensation products in good yields.Successive reaction of 1 with electrophiles and nucleophiles provided a convenient route to 1,3-disubstituted indole derivatives.Keywords-conjugated enamine; 3-indolecarbaldehyde; 3-(aminomethylene)-3H-indole; 3-(aminomethylene)-3H-indolium salt; active methylene compounds; 3-(substituted vinyl)indole; gramine; electrophilic reaction; condensation