6328-61-6

Usage

Uses

Used in Organic Synthesis:
(diphenylmethyl)(trimethyl)silane is used as a reagent for the introduction of the trimethylsilyl group in various organic reactions. It aids in the formation of carbon-carbon bonds and the protection of functional groups, enhancing the efficiency and selectivity of synthetic processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (diphenylmethyl)(trimethyl)silane is utilized as a protecting group for certain functional groups in drug molecules, facilitating their synthesis and purification.
Used in Silicone Polymer Production:
(diphenylmethyl)(trimethyl)silane is employed as a building block in the production of silicone polymers, which are essential materials in various applications, including medical devices, sealants, and coatings.
Used as a Crosslinking Agent in Resins and Plastics:
In the plastics and resins manufacturing industry, (diphenylmethyl)(trimethyl)silane is used as a crosslinking agent. It helps improve the mechanical properties, thermal stability, and durability of the final products.
Safety and Handling:
Due to the reactivity and potential hazards associated with (diphenylmethyl)(trimethyl)silane, it is crucial to follow proper handling and storage protocols to ensure safety and prevent accidents. This includes using appropriate containment, ventilation, and protective equipment during its use in laboratories and industrial settings.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 18089-94-6 (diphenylmethyl)trichlorosilane 
• 75-77-4 chloro-trimethyl-silane 
• 101-81-5 Diphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 
• 86-29-3 Diphenylacetonitrile 
• 42451-53-6 triethyl(1,1-diphenylmethoxy)silane 
• 95-14-7 1,2,3-Benzotriazole 
• 776-74-9 Bromodiphenylmethane 
• 74-85-1 ethene 
• 881-42-5 diphenylmethyllithium 
• 85316-26-3 3,3-diphenylpropyllithium 
• 591-50-4 iodobenzene 
• 960-16-7 tributylphenylstannane 

Downstream Products

• 17922-21-3 (α-bromo-benzhydryl)-trimethyl-silane 
• 101-81-5 Diphenylmethane 
• 56859-55-3 (2,2,2-trifluoroethoxy)trimethylsilane 
• 81290-17-7 1,1-diphenyl-3-trimethylsilylpropane 
• 81290-07-5 1-trimethylsilyl-1,1,2-triphenylethane 
• 127725-90-0 Benzhydryl-bromo-dimethyl-silane 
• 859315-37-0 1-bromo-4-(1-(4-bromophenyl)-2,2-diphenylvinyl)benzene 
• 68161-05-7 4,4'-(2,2-diphenylethene-1,1-diyl)bis(methoxybenzene) 

Relevant academic research and scientific papers

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

Metal-free synthesis of gem -silylboronate esters and their Pd(0)-catalyzed cross-coupling with aryliodides

A transition-metal-free method for the synthesis of gem-silylboronate esters with arylboronic acids and trimethylsilyldiazomethane (TMSCHN2) has been developed. This transformation is a straightforward homologation of arylboronic acids and features wide substrate scope and good functional-group tolerance. The gem-silylboronate esters undergo efficient Suzuki-Miyaura cross-coupling with aryliodides and the silyl group of the product can be further functionalized. Tertiary carbon centers with different substituents can be constructed successfully by selective and sequential functionalization.

Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds

A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.

Dications of fluorenylidenes. The relationship between redox potentials and antiaromaticity for meta- and para-substituted diphenylmethylidenefluorenes

Electrochemical oxidation of meta-substituted diphenylmethylidenefluorenes (3a-g) results in the formation of fluorenylidene dications that are shown to be antiaromatic through calculation of the nucleus independent chemical shift (NICS) for the 5- and 6-

Palladium-catalyzed insertion reactions of trimethylsilyldiazomethane

Palladium(II) salts catalyze the Kirmse reaction of allylsulfides with trimethylsilyldiazomethane (TMSD) to give homoallylsulfides. Similarly, TMSD can intercept ArPdX intermediates generated during Stille couplings to give benzhydryl derivatives. The yie

Nanosecond laser flash photolysis and steady-state photolysis studies of benzyltrimethylsilane and trimethylsilyldiphenylmethane

Flourescence measurements and nanosecond laser flash photolysis were carried out to study the photophysical and photochemical processes of benzyltrimethylsilane and trimethylsilyldiphenylmethane at room temperature. A significant solvent effect was observed for the laser flash photolysis of benzyltrimethylene; in methanol, absorption bands due to benzyl-type radicals and the triplet were seen, while only T-T absorption was observed in cyclohexane. No solvent effect was found for the laser flash photolysis of trimethylsilyldiphenylmethane. A transient absorption attributable to the 1,3-trimethylsilyl-shifted intermediate was seen with a lifetime of ca. 27 ms in both solvents, and no absorption band ascribable to diphenylmethyl radicals or the triplet was observed. GC-MS spectra of photoproducts caused by trimethylsilyldiphenylmethane were consistent with the assignment of the transient absorption. Results were explained in terms of the computed molecular structure for the excited singlet states of the molecules using the PM3 method.

Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C-Benzotriazole Bond Scission

Various TV-substituted benzotriazoles are transformed, by scission of the C-benzotriazole bond, into the corresponding carbanions by treatment with lithium. Thus, N-(diphenylmethyl)benzotriazole (1), N-benzylbenzotriazole (6), and N-allylbenzotriazole (10) all gave carbanions that reacted with diverse electrophiles to afford the corresponding products in good yields. This new methodology was successfully utilized to convert N-benzylbenzotriazole (6) and N-allylbenzotriazole (10) into dianion synthons by a sequential lithiation and reductive coupling and bis(benzotriazolyl)toluene (18) by double reductive couplings, demonstrating the synthetic potential of the present methodology.

Carbanion Rearrangements by Intramolecular 1,ω Proton Shifts, IV. The Reaction of ω,ω-Diphenylalkyllithium Compounds: Proof for an Intramolecular Transmetallation Reaction by Crossover Experiments Using Isotopic Labelled Starting Material

3,3-Diphenylpropyllithium (2) and 2-(9-fluorenyl)ethyllithium (43) do not show a 1,3 proton shift but splitt off ethylene.On the other hand 4,4-diphenylbutyllithium (19) in diethyl ether can be forced to rearrange to 1,1-diphenylbutyllithium (18) by the addition of THF.The half reaction time for this 1,4 proton shift was found to be about 4 minutes.Proof for the intramolecular character of this transmetallation reaction was obtained by crossover experiments with specifically deuterated starting material.The 1,5 proton shift with 5,5-diphenylpentyllithium (12) occurs considerably slower than the 1,4 shift with 4,4-diphenylbutyllithium (19).The rearrangement also takes place in pure diethyl ether although with a half reaction time of about 2 days.Only 3-(9-fluorenyl)propyllithium (41) in diethyl ether spontaneously shows rearrangement already at -30 deg C, whereby 9-propyl-9-fluorenyllithium (42) is formed by a 1,4 proton shift.A 1,ω phenyl migration according to Grovenstein-Zimmerman in no case could be observed.

1,n-TRIORGANOSILYL MIGRATIONS IN THE REARRANGEMENTS OF SILYL-SUBSTITUTED ORGANOLITHIUM COMPOUNDS

Under the agency of the potent lithiating agent, n-butyllithium in TMEDA, an array of organosilanes was found to undergo 1,n-silyl rearangements via carbanionic intermediates.Unambiguous 1,2-, 1,3- and 1,4-silyl shifts were unconvered in 1-trimethylsilyl-