75174-08-2

Basic information

• Product Name: tert-butyldimethylsilyl (phenylmethylene)azinate
• CAS NO: 75174-08-2
• Molecular Weight: 251.401
• Mol File: 75174-08-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: tert-butyldimethylsilyl (phenylmethylene)azinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyldimethylsilyl (phenylmethylene)azinate(75174-08-2)
• EPA Substance Registry System: tert-butyldimethylsilyl (phenylmethylene)azinate(75174-08-2)

Safety Data

• Hazardous Substances Data: 75174-08-2(Hazardous Substances Data)

Upstream product

• 622-42-4 1-nitro-1-phenylmethane 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 259150-97-5 Methyl 3-phenyl-1,2,4-oxadiazole-5-carboxylate 
• 133683-79-1 4,4-Dimethyl-1-nitro-1-phenyl-pentan-3-one 
• 133683-81-5 4-((Z)-1-tert-Butyl-3-nitro-3-phenyl-propenyl)-morpholine 
• 133683-80-4 4-(5-tert-Butyl-2-oxy-3-phenyl-4,5-dihydro-isoxazol-5-yl)-morpholine 
• 588-59-0 stilbene 
• 67765-80-4 (+/-)-1,2-dinitro-1,2-diphenylethane 
• 94-41-7 benzalacetophenone 

Relevant articles and documents

Metal-Catalyzed Synthesis of Functionalized 1,2,4-Oxadiazoles from Silyl Nitronates and Nitriles

The metal-catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4-oxadiazoles is described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf)3] are suitable catalysts. A variety of functional groups is tolerated in the nitrile. The reaction works well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert-butyl(dimethyl)silanol (TBSOH) after the cycloaddition step. The new approach has also been applied for the synthesis of the drug ataluren. (Figure presented.).