1449612-21-8

Basic information

• Product Name: (Z)-2-{4-[(4-fluorophenyl)imino]-2-phenyl-1H-imidazol-5(4H)-ylidene}malononitrile
• Synonyms: (Z)-2-{4-[(4-fluorophenyl)imino]-2-phenyl-1H-imidazol-5(4H)-ylidene}malononitrile
• CAS NO: 1449612-21-8
• Molecular Weight: 315.309
• Mol File: 1449612-21-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-2-{4-[(4-fluorophenyl)imino]-2-phenyl-1H-imidazol-5(4H)-ylidene}malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-{4-[(4-fluorophenyl)imino]-2-phenyl-1H-imidazol-5(4H)-ylidene}malononitrile(1449612-21-8)
• EPA Substance Registry System: (Z)-2-{4-[(4-fluorophenyl)imino]-2-phenyl-1H-imidazol-5(4H)-ylidene}malononitrile(1449612-21-8)

Safety Data

• Hazardous Substances Data: 1449612-21-8(Hazardous Substances Data)

Upstream product

• 21719-88-0 N′-(4-fluorophenyl)benzamidine 
• 670-54-2 ethenetetracarbonitrile 
• 1449612-12-7 N′-(4-fluorophenyl)-N-(1,2,2-tricyanovinyl)benzamidine 

Downstream Products

• 1449576-68-4 7-fluoro-2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitrile 

Relevant articles and documents

Reactions of tetracyanoethylene with N′-arylbenzamidines: A route to 2-phenyl-3 H -imidazo[4,5- b ]quinoline-9-carbonitriles

Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N′-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ～70-90% yields. The transformation involves the initial formation of N-aryl-N′-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H- imidazol-4(5H)-ylidene]malononitriles 13 in 84-92% yields, while in MeOH the (Z)-2-[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85-94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations.