18753-27-0

Basic information

• Product Name: 1,4-bis(dimethyl(phenyl)silyl)benzene
• Synonyms: 1,4-bis(dimethyl(phenyl)silyl)benzene
• CAS NO: 18753-27-0
• Molecular Weight: 346.619
• Mol File: 18753-27-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,4-bis(dimethyl(phenyl)silyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(dimethyl(phenyl)silyl)benzene(18753-27-0)
• EPA Substance Registry System: 1,4-bis(dimethyl(phenyl)silyl)benzene(18753-27-0)

Safety Data

• Hazardous Substances Data: 18753-27-0(Hazardous Substances Data)

Upstream product

• 540-36-3 para-difluorobenzene 
• 768-33-2 phenyldimethylsilyl chloride 
• 2488-01-9 1,4-bis(dimethylsilyl)benzene 
• 71-43-2 benzene 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 56-33-7 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane 
• 1145-98-8 1,2-diphenyltetramethyldisilane 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 27607-78-9 bis(trifluoromethanesulfonyloxy)dimethylsilane 

Relevant articles and documents

Silyldefluorination of Fluoroarenes by Concerted Nucleophilic Aromatic Substitution

The reaction of readily generated silyl lithium reagents with various aryl fluorides to provide the corresponding aryl silanes is reported. DFT calculations reveal that the nucleophilic aromatic substitution of the fluoride anion by the silyl lithium reagent proceeds through concerted ipso substitution. In contrast to the classical nucleophilic aromatic substitution, this concerted ionic silyldefluorination also occurs on more electron-rich aryl fluorides.

The preparation and analysis of the phenyldimethylsilyllithium reagent and its reaction with silyl enol ethers

Phenyldimethylsilyllithium is formed from lithium and phenyldimethylsilyl chloride by slow cleavage of the Si-Si bond of 1,1,2,2-tetramethyl-1,2-diphenyldisilane after the rapid formation of the disilane. 1,1,2,2-Tetramethyl-1,2-diphenyldisiloxane, produced from the silyl chloride by reaction with oxides and hydroxides on the lithium metal surface, is cleaved by dimethyl(phenyl)silyllithium to give lithium dimethyl(phenyl)silanoxide. Dimethyl(phenyl)silyllithium reacts with 1,2-dibromoethane to give dimethyl(phenyl)silyl bromide, which is so rapidly consumed by excess silyllithium reagent that it does not interfere with the double titration used to measure its concentration. Dimethyl(phenyl)silane, produced by protonation of the silyllithium reagent, is also consumed by the silyllithium reagent to give 1,1,2,2-tetramethyl-1,2-diphenyldisilane, which regenerates the silyllithium reagent, as long as lithium is still present. By-products in the preparation of dimethyl(phenyl)silyllithium include 1,3-diphenyl-1,1,2,2,3,3-hexamethyltrisilane, dimethyldiphenylsilane and 1,4-bis[dimethyl(phenyl)-silyl]benzene. Dimethyl(phenyl)silyllithium displaces the silyl group from the tert-butyldimethylsilyl enol ether of cyclohexanone to give the lithium enolate under relatively mild conditions.