104944-99-2

Basic information

• Product Name: Benzene, [[(1Z)-1,2-dichloroethenyl]seleno]-
• CAS NO: 104944-99-2
• Molecular Formula: C8H6Cl2Se
• Molecular Weight: 252.002
• Mol File: 104944-99-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, [[(1Z)-1,2-dichloroethenyl]seleno]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [[(1Z)-1,2-dichloroethenyl]seleno]-(104944-99-2)
• EPA Substance Registry System: Benzene, [[(1Z)-1,2-dichloroethenyl]seleno]-(104944-99-2)

Safety Data

• Hazardous Substances Data: 104944-99-2(Hazardous Substances Data)

Upstream product

• 127-18-4 1,1,2,2-tetrachloroethylene 
• 645-96-5 Benzeneselenol 
• 7572-29-4 dichloroethyne 
• 79-01-6 Trichloroethylene 
• 23616-79-7 benzyltri(n-butyl)ammonium chloride 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 116525-22-5 E-phenyl α,β-dichlorovinyl selenide 

Relevant articles and documents

Chlorovinylation of diphenyl dichalcogenides with dichloroacetylene-A new method of synthesis of 1,2-dichlorovinyl phenyl chalcogenides

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CHLOROVINYLATION OF BENZENESELENOL AND ORGANIC DISELENIDES BY CHLORO- AND DICHLOROACETYLENES

Mixtures of the Z and E isomers of unsaturated organic selenides and 1,2-bis(organoseleno)mono(di)chloroethylenes were obtained by the addition of benzeneselenol and organic diselenides to the etherates of chloro- and dichloroacetylene

REACTION OF BENZENESELENOL WITH TRI- AND TETRACHLOROETHYLENES UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS

The reaction of benzeneselenol with trichloroethylene in concentrated sodium hydroxide solution, catalyzed by ammonium salts, leads to Z-phenyl α,β-dichlorovinyl selenide with an equimolar ratio of the catalyst and the selenol or to a mixture of the Z and E isomers with a ratio of 1:10.In addition to the expected trichlorovinyl selenide PhSeCCl=CCl2, the analogous reaction with tetrachloroethylene also gives a mixture of the Z and E isomers of α,β-dichlorovinyl selenides and, in addition, 1,2-bis(phenylseleno)-1,2-dichloroethylene PhSeCCl=CClSePh.If trialkylbenzylammonium chlorides R3PhCH2N(1+)*Cl(1-) are used as catalyst, phenyl benzyl selenide PhSeCH2Ph is formed as a side product.The results of the reaction in the case of trichloroethylene are explained by the addition of the selenolate ion to the CClCCl, generated from the trichloroethylene in situ, and isomerization of the initially formed Z-phenyl α,β-dichlorovinyl selenide to the thermodynamically more stable E isomer.In the case of tetrachloroethylene they are explained by the usual addition-elimination mechanism with the formation of trichlorovinyl selenide, accompanied by reductive dechlorination of the CCl2=CCl2 to CHCl=CCl2 by the selenolate and subsequent reaction of the selenolate with CHCl=CCl2.