20343-91-3

Basic information

• Product Name: bis(p-tolylseleno)methane
• Synonyms: bis(p-tolylseleno)methane
• CAS NO: 20343-91-3
• Molecular Weight: 354.212
• Mol File: 20343-91-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: bis(p-tolylseleno)methane(CAS DataBase Reference)
• NIST Chemistry Reference: bis(p-tolylseleno)methane(20343-91-3)
• EPA Substance Registry System: bis(p-tolylseleno)methane(20343-91-3)

Safety Data

• Hazardous Substances Data: 20343-91-3(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 30876-65-4 2-phenyl-1-(phenylseleno)ethanone 
• 104722-87-4 Se-(4-methylphenyl) ethaneselenoate 
• 107-30-2 chloromethyl methyl ether 
• 104722-86-3 Se-p-tolyl 2-(phenyl)-selenoacetate 
• 21856-94-0 di-p-tolyl diselenide 

Downstream Products

• 171615-35-3 2-Phenyl-1,1-bis-(p-tolylseleno)ethane 

Relevant articles and documents

REACTION OF DIAZOMETHANE WITH SELENOESTERS PREPARATION OF α-(ALKYL- OR ARYLSELENO)METHYL KETONES AND METHYL KETONES

The reaction of diazomethane with a series of selenoesters 1 in the presence of CuI, CuSePh or Cu powder produced α-(alkyl- or arylseleno)methyl ketones 2 in yield of 41-65percent.Methyl ketones 3 and bis(arylseleno)methanes 9 or 14 were formed as by-products.The direct conversion of selenoesters to methyl ketones was accomplished in high yield by the usual reaction with diazomethane, followed by workup with HBr solution.The simultaneous copper-catalyzed reactions of selenoesters 1c and 1i with diazomethane resulted in crossover, with the formation of all four possible α-seleno ketones 2b, 2c, 2h and 2i.A non-concerted mechanism involving attack by the diazo compound upon the acyl carbon atom of an activated selenoester with the formation of a tetrahedral intermediate 11 has been suggested.The reaction of the selenothiocarbamate 4 with diazomethane resulted in 1,3-dipolar cycloaddition to afford 5 instead of insertion into the acyl-selenium bond.