79158-51-3

Basic information

• Product Name: Benzene, 1,1'-[1-chloro-2-(chloromethyl)-1,2-ethenediyl]bis-, (E)-
• CAS NO: 79158-51-3
• Molecular Formula: C15H12Cl2
• Molecular Weight: 263.166
• Mol File: 79158-51-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[1-chloro-2-(chloromethyl)-1,2-ethenediyl]bis-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[1-chloro-2-(chloromethyl)-1,2-ethenediyl]bis-, (E)-(79158-51-3)
• EPA Substance Registry System: Benzene, 1,1'-[1-chloro-2-(chloromethyl)-1,2-ethenediyl]bis-, (E)-(79158-51-3)

Safety Data

• Hazardous Substances Data: 79158-51-3(Hazardous Substances Data)

Upstream product

• 501-65-5 diphenyl acetylene 
• 3188-13-4 ethyl chloromethyl ether 
• 107-30-2 chloromethyl methyl ether 
• 4452-11-3 1,2-diphenylprop-2-en-1-one 

Downstream Products

• 79158-54-6 2-Chloromethyl-2,3-diphenyl-2H-azirine 
• 79158-56-8 C₁₅H₁₂ClN₃ 

Relevant articles and documents

ELECTROPHILIC ADDITION TO ACETYLENES. VIII. STEREOCHEMISTRY OF THE ADDITION OF ALKYL CHLOROMETHYL ETHERS TO PHENYL-SUBSTITUTED ALKYNES

The zinc-chloride-catalyzed addition of chloromethyl ethyl ether and chloromethyl methyl ether to some phenyl alkynes and to 2-butyne in dichloromethane was studied.In most cases the reactions afforded mixtures of the 1:1 addition products and of the corresponding dichloro derivatives, in which the allylic alkoxyl group was replaced by a chloro atom.The characteristics of the reaction and the stereochemistry of the addition are consistent with a stepwise electrophilic addition mechanism, with formation of vinyl cations by attack of alkoxy-substituted carbenium ions to the triple bond and subsequent preferential attack by the nucleophile Cl- on the less hindered side of the intermediates.However, at variance with previous studies, E-Z isomerization of the addition products under the reaction conditions was observed, which made less clear-cut the stereochemical data.This isomerization reaction and the formation of dichloro derivatives are explained in terms of a subsequent reaction of the 1:1 addition products with the alkyl chloromethyl ether, through the intermediacy of γ-phenyl-substituted allylic cations.