3559-72-6

Basic information

• Product Name: Benzene, [(2,2-dichloroethenyl)thio]-
• CAS NO: 3559-72-6
• Molecular Formula: C8H6Cl2S
• Molecular Weight: 205.108
• Mol File: 3559-72-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, [(2,2-dichloroethenyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(2,2-dichloroethenyl)thio]-(3559-72-6)
• EPA Substance Registry System: Benzene, [(2,2-dichloroethenyl)thio]-(3559-72-6)

Safety Data

• Hazardous Substances Data: 3559-72-6(Hazardous Substances Data)

Upstream product

• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 79-01-6 Trichloroethylene 
• 882-33-7 diphenyldisulfane 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 56354-48-4 2,2,2-trichloroethyl phenyl sulfide 
• 20163-53-5 phenyl-(1,2,2,2-tetrachloro-ethyl)-sulfide 

Downstream Products

• 79894-50-1 tert-butoxyethynyl phenyl sulfide 
• 6228-98-4 phenylthioacetylene 
• 1886-64-2 3,3-dimethylbut-1-en-2-yl phenyl sulfide 
• 79894-52-3 (chloroethynyl)(phenyl)sulfane 
• 13061-73-9 7-Chloro-8-phenylsulfonyl-dibenzobicyclo<2.2.2>octatrien 
• 127492-03-9 1-(phenylsulfinyl)-2,2,2-triethoxyethane 
• 106488-47-5 (phenylthioethynyl)triphenylphosphonium chloride 
• 83188-29-8 methyl 1-((phenylthio)ethynyl)cyclohexanecarboxylate 
• 83188-18-5 2,6-dimethyl-6-((phenylthio)ethynyl)-2-cyclohexen-1-one 
• 83188-32-3 ethyl 2,2-dimethyl-4-(phenylthio)but-3-ynoate 
• 83188-28-7 3,3,5-trimethyl-1-(phenylthio)hex-1-yn-4-one 
• 97427-17-3 2-(phenylthiomethylene)-3,3-dimethyl-1,3-oxazolidinium chloride 
• 96204-67-0 C₂₀H₁₄N₂O₅S₃ 
• 14090-83-6 methyl 2-phenylsulfinylacetate 

Relevant articles and documents

A New Approach to the Synthesis of Symmetrical Bis(organylchalcogeno)acetylenes: Scope and Limitations

A new general method to prepare bis(organylchalcogeno)acetylenes R-Y-CC-Y-R (Y = S, Se, Te) by dehydrochlorination of the corresponding 1,2-bis(organylchalcogeno)chloroethylenes R-Y-CH=CCl-Y-R with tert-BuOK/tert-BuOH and/or KOH/DMSO is developed.Dechlorination of 1,2-bis(organylchalcogeno)-1,2-dichloroethylenes R-Y-CCl=CCl-Y-R (Y = S, Se, Te) with BuLi in ether or THF is effective only for sulfur derivatives.With Y = Se and alkyl substituents, substitution of the chlorine atom by a butyl group takes place giving rise to 5,6-bis(alkylseleno)dec-5-ene .With aryl substituents, an attack of the ArSe-group by the Bu-radical is observed leading to an aryl butyl selenide.In the case of the tellurium compound Ph-Te-CCl=CCl-Te-Ph, there is a competition between dechlorination to give Ph-Te-CC-Te-Ph, and substitution to produce the phenyl butyl telluride. - Keywords: bis(organylchalcogeno)acetylene; 1,2-bis(organylchalcogeno)chloroethylene; 1,2-bis(organochalcogeno)-1,2-dichloroethylene.

FREE-RADICAL REACTION OF ARENETHIOLS WITH TETRACHLOROETHYLENE

The reaction of arenethiols ArSH (Ar = p-Tol, Ph, 4-ClC6H4) with tetrachloroethylene, initiated by UV irradiation or benzoyl peroxide, leads to the formation of mixtures of unsaturated and saturated products, i.e., aryl α,β-dichlorovinyl and β,β-dichlorovinyl sulfides, trichlorovinyl sulfides, 1,1,2,2-tetrachloroethyl and 1,2,2,2-tetrachloroethyl sulfides, diaryl disulfides, and isomeric diarylthiodichloroethenes.During discussion of the reaction mechanism, which involves reaction of the ArS radical with the tetrachloroethylene, evidence is given in favor of an α,β-chlorotropic rearrangement of the intermediate radical ArSCCl2CCl2 to the radical ArSCClCCl3.After the appropriate treatment it is possible to isolate the aryl trichlorovinyl sulfides in a mixture with small amount of aryl α,β-dichlorovinyl and aryl β,β-dichlorovinyl sulfides.

SYNTHESES AND REACTIONS OF PHENYLTHIO AND PROPYLTHIOACETYLENIC COMPOUNDS

Reactions of 2,2-dichlorovinyl sulfides and their sulfoxide and sulfone derivatives with tert-butoxide and with organolithium compounds have provided entries to chloroethynyl sulides, tert-butoxyethynyl sulfides and their derivatives.Application of these reactions for the synthesis of several functional derivatives is also described.Keywords: 2,2-dichlorovinyl sulfide; chloroethynyl sulfide; tert-butoxyethynyl sulfide; ethynyl sulfide; cyclobutenone