115444-36-5

Usage

Common Use

Building block for organic synthesis

Physical State

Stable, colorless liquid

Reactivity

Highly reactive due to multiple functional groups

Key Functionality

Formation of carbon-silicon bonds

Applications

a. Production of silicon-based materials
b. Development of pharmaceuticals and agrochemicals
c. Creation of advanced materials for electronic applications

Importance

Versatile and reactive compound in organic chemistry

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 1145-98-8 1,2-diphenyltetramethyldisilane 

Downstream Products

• 799-35-9 1,1,2,2,3,3,4,4-octamethyl-1,4-diphenyltetrasilane 
• 60933-18-8 diethylammonium trifluoromethanesulfonate 
• 36112-13-7 1,1,2,2-tetramethyl-1,2-bis(p-trifluoromethylphenyl)silane 
• 10536-64-8 sym. Bis-<4-dimethylamino-phenyl>-tetramethyl-disilan 
• 5971-96-0 1,1,2,2-tetramethyl-1,2-bis(4-tolyl)disilane 
• 6009-50-3 1,2-di-p-methoxyphenyl-1,1,2,2-tetramethyldisilane 
• 10124-62-6 1,2-dimethoxy-1,1,2,2-tetramethyldisilane 

Relevant academic research and scientific papers

Synthesis and reactions of silanes containing two triflate groups

1,2-Bis(trifluoromethanesulfonyloxy)tetramethyldisilane (1) and dimethylsilylbis(trifluoromethanesulfonate) (2) have been prepared via displacement of phenyl, chloro, and methyl groups in the corresponding mono- and di-silanes.Phenyl groups are displaced more rapidly than chloro and methyl groups.The unreacted groups are strongly deactivated by the presence of a triflate group at the same silicon atom.The deactivation is much weaker when a triflate group is present at the adjacent silicon atom.Alcohols and amines react more rapidly with ditriflates than with monotriflates.

Dearylation of α,ω-diphenylpermethylated oligosilanes with triflic acid

The relative rates of displacement of phenyl groups for a series of α,ω-diphenylpermethylated oligosilanes with the formula Ph(SiMe2)nPh (n = 2-5) were studied.Triflic acid was utilized in the displacement reactions which occur as a two-step process with protonation at the ipso-carbon atom as the rate limiting step.The results showed the displacement of the first phenyl group is more facile than the second group.The largest difference in reactivities is found for the disilane.Competitive displacement reactions between various oligomers were analyzed to establish the influence of the chain length of oligosilanes on the relative reactivities of the terminal phenyl groups.Both the first and second phenyl group displacement reactions are faster for the longer chain oligomers than the shorter analogs.The 13C NMR spectra of the oligosilanes indicate the highest electron density on the ipso-carbon atoms in the disilane, in contrast to its lowest reactivity.This is interpreted by the increased stabilization of the positive charge in the transition state with an increase in the chain length.Thus, the reactivities of oligosilanes are governed by the structures of the transition states rather than the ground states.