370558-15-9

Basic information

• Product Name: N-(2-iodo-4-methylphenyl)-N-ethylcinnamide
• CAS NO: 370558-15-9
• Molecular Weight: 391.252
• Mol File: 370558-15-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(2-iodo-4-methylphenyl)-N-ethylcinnamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-iodo-4-methylphenyl)-N-ethylcinnamide(370558-15-9)
• EPA Substance Registry System: N-(2-iodo-4-methylphenyl)-N-ethylcinnamide(370558-15-9)

Safety Data

• Hazardous Substances Data: 370558-15-9(Hazardous Substances Data)

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 29289-13-2 2-iodo-4-methylaniline 
• 74-96-4 ethyl bromide 
• 370558-13-7 N-(2-iodo-4-methylphenyl)cinnamamide 

Relevant articles and documents

Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation

In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.