15297-70-8

Basic information

• Product Name: (2S*,3R*)-1,2-dicyano-1-phenylpropane
• CAS NO: 15297-70-8
• Molecular Weight: 170.214
• Mol File: 15297-70-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S*,3R*)-1,2-dicyano-1-phenylpropane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S*,3R*)-1,2-dicyano-1-phenylpropane(15297-70-8)
• EPA Substance Registry System: (2S*,3R*)-1,2-dicyano-1-phenylpropane(15297-70-8)

Safety Data

• Hazardous Substances Data: 15297-70-8(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 100-52-7 benzaldehyde 
• 107154-18-7 2,3-dicyano-3-phenyl-propionic acid tert-butyl ester 
• 74-88-4 methyl iodide 
• 532-28-5 (RS)-mandelonitrile 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 18734-79-7 (SR,RS)-2-methyl-3-phenylsuccinic acid 
• 18734-79-7 (SR,SR)-2-methyl-3-phenylsuccinic acid 

Relevant articles and documents

Straightforward synthesis of 1,2-dicyanoalkanes from nitroalkenes and silyl cyanide mediated by tetrabutylammonium fluoride

A straightforward synthesis of 1,2-dicyanoalkanes by reacting nitroalkenes with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride is described. The reaction proceeds through a tandem double Michael addition under mild conditions. Employing the hypervalent silicate generated from trimethylsilyl cyanide and tetrabutylammonium fluoride is essential for achieving this transformation. Mechanistic studies suggest that a small amount of water included in the reaction media plays a key role. This protocol is applicable to various types of substrates including electron-rich and electron-deficient aromatic nitroalkenes, and aliphatic nitroalkenes. Moreover, vinyl sulfones were found to be good alternatives, particularly for electron-deficient nitroalkenes. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 1,2-dicyanoalkanes.