791-29-7

Usage

Uses

Used in Organic Chemistry:
Methyltriphenylsilane is used as a reducing agent for the conversion of carbonyl compounds to alcohols, facilitating various organic synthesis processes.
Used in Synthesis of Silicon-Containing Compounds:
It serves as a key component in the creation of a variety of silicon-containing compounds, contributing to the advancement of materials science and chemical research.
Used as a Precursor for Organosilanes Production:
Methyltriphenylsilane is employed as a precursor in the production of other organosilanes, which are essential in numerous industrial applications, including the manufacturing of resins, polymers, and silicone-based products.

InChI:InChI=1/C19H18Si/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h2-16H,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 76-86-8 Triphenylsilyl chloride 
• 776-76-1 methyldiphenylsilane 
• 2031-67-6 Methyltriethoxysilan 
• 591-51-5 phenyllithium 
• 75-79-6 Methyltrichlorosilane 
• 108-90-7 chlorobenzene 
• 917-54-4 methyllithium 
• 789-25-3 HSiPh₃ 
• 75-16-1 methylmagnesium bromide 
• 75-54-7 Dichloromethylsilane 
• 108-86-1 bromobenzene 
• 144-79-6 chloromethyldiphenylsilane 
• 102129-44-2 sodium bis(1,2-benzenediolato)methylsilicate 

Downstream Products

• 1626-24-0 chlorotriphenylgermane 
• 1074-29-9 trichlorophenylgermane 
• 1613-66-7 dichlorodiphenylgermane 
• 791-31-1 triphenylhydroxysilane 
• 2117-32-0 n-butyl(triphenyl)silane 
• 1048-08-4 tetraphenylsilane 
• 10090-04-7 (Methyl-diphenyl-silyl)-benzolsulfonat 
• 3857-04-3 [18F]fluorobenzene 
• 18678-59-6 (CCl₃)Siph₃ 
• 18662-94-7 tricyclohexyl-methyl-silane 

Relevant academic research and scientific papers

Crystal structures of the chiral diamine (R,R)-TMCDA with the commonly used alkyllithium bases methyllithium, iso-propyllithium, and sec-butyllithium

(R,R)-N,N,N′,N′-Tetramethyl-1,2-diaminocyclohexane [(R,R)-TMCDA] coordinated alkyllithiums crystallize as dimeric [MeLi·(R,R)-TMCDA]2 and [i-PrLi·(R,R)-TMCDA]2 and monomeric s-BuLi·(R,R)-TMCDA. s-BuLi·(R,R)-TMCDA is the first structu

Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide

We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.

METHOD FOR PRODUCING ARYLSILANE COMPOUND CONTAINING HALOSILANE COMPOUND AS RAW MATERIAL

PROBLEM TO BE SOLVED: To provide a method for producing an arylsilane compound with low production cost. SOLUTION: A method for producing an arylsilane compound includes a reaction step for the cross-coupling reaction of a halosilane compound represented by general formula (A-1), (A-2), or (A-3) and an arylboronic acid pinacol ester in the presence of a nickel catalyst, a Lewis acid catalyst, and an organic base (R independently represent an aromatic hydrocarbon group, a heteroaromatic ring group, or a C1-20 hydrocarbon group; X independently represent a halogeno group or a trifluoromethanesulfonyloxy group). SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Nickel-Catalyzed Decarbonylation of Acylsilanes

Nickel-catalyzed decarbonylation of acylsilanes is developed. In sharp contrast to cross-coupling reactions of acylsilanes, in which the silyl group serves as a leaving group, the silyl group is retained in the product in this decarbonylation reaction. Although the strong binding of the dissociated CO to the nickel center frequently hinders catalyst turnover in nickel-mediated decarbonylative reactions, this reaction can be catalyzed by nickel complexes bearing a CO ligand.

Dimethylformamide-stabilised palladium nanoclusters catalysed coupling reactions of aryl halides with hydrosilanes/disilanes

N,N-Dimethylformamide-stabilised Pd nanocluster (NC) catalysed cross-coupling reactions of hydrosilane/disilane have been investigated. In this reaction, the coupling reaction proceeds without ligands with low catalyst loading. N,N-Dimethylacetamide is a crucial solvent in these reactions. The solvent effect was considered by various techniques, such as transmission electron microscopy, X-ray photoelectron spectroscopy, and thermogravimetric analysis. The Pd NCs can be recycled five times under both hydrosilane and disilane reaction conditions.

A well-defined NHC-Ir(III) catalyst for the silylation of aromatic C-H bonds: Substrate survey and mechanistic insights

A well-defined NHC-Ir(iii) catalyst, [Ir(H)2(IPr)(py)3][BF4] (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene), that provides access to a wide range of aryl- and heteroaryl-silanes by intermolecular dehydrogenative C-H bond silylation has been prepared and fully characterized. The directed and non-directed functionalisation of C-H bonds has been accomplished successfully using an arene as the limiting reagent and a variety of hydrosilanes in excess, including Et3SiH, Ph2MeSiH, PhMe2SiH, Ph3SiH and (EtO)3SiH. Examples that show unexpected selectivity patterns that stem from the presence of aromatic substituents in hydrosilanes are also presented. The selective bisarylation of bis(hydrosilane)s by directed or non-directed silylation of C-H bonds is also reported herein. Theoretical calculations at the DFT level shed light on the intermediate species in the catalytic cycle and the role played by the ligand system on the Ir(iii)/Ir(i) mechanism.

Direct Introduction of a Dimesitylboryl Group Using Base-Mediated Substitution of Aryl Halides with Silyldimesitylborane

The first dimesitylboryl substitution of aryl halides with a silylborane bearing a dimesitylboryl group in the presence of alkali-metal alkoxides is described. The reactions of aryl bromides or iodides with Ph2MeSi?BMes2and Na(OtBu) afforded the desired aryl dimesitylboranes in good to high yields and with high borylation/silylation ratios. Selective reaction of the sterically less-hindered C?Br bond of dibromoarenes provided monoborylated products. This reaction was used to rapidly construct a D-π-A aryl dimesityl borane with a non-symmetrical biphenyl spacer.

On the reactivity of silylboranes toward lewis bases: Heterolytic B-Si cleavage vs. adduct formation

Silylboranes are important reagents in a variety of catalytic silylation and silaboration reactions. While transition-metal-catalyzed reactions are well established, organo-/Lewis base-catalyzed reactions of silylboranes have only recently emerged. For both catalytic processes the reactivity of silylboranes toward Lewis bases is of relevance. While for organo-catalyzed reactions Lewis base activation of the silylborane has been proposed, transition-metal- and especially copper-catalyzed reactions also frequently require the presence of Lewis basic alkali metal alkoxides. In the present study we explore the reaction of K(18-crown-6) tert-butoxide and the NHC 1,3-diisopropyl-4,5-dimethyl- imidazol-2-ylidene as exemplary Lewis bases with the two silylboranes pinB-SiMe2Ph and pinB-SiPh3 (pin = OCMe 2CMe2O). The reaction with K(18-crown-6) tert-butoxide results in activation of the boron-silicon bond. The isolated product of this activation is either the potassium silyl complex [K(18-crown-6)SiPh3] or [K(18-crown-6)(thf)2][pinB(SiMe2Ph)2], the formal Lewis acid/base adduct of [K(18-crown-6)SiMe2Ph] with pinB-SiMe2Ph. Both complexes react essentially as sources of nucleophilic silyl moieties in reactions with exemplary electrophiles. In contrast, usage of the carbene leads to the formation of isolable Lewis acid/base adducts of the type (NHC)pinB-SiR3, which do not react as sources of nucleophilic silyl moieties. The identification and characterization of these species appears of relevance for the mechanistic understanding and further development of Lewis base/organo- as well as transition-metal-catalyzed silyl transfer reactions. Copyright

Preferential carbene insertion into Ge-H vs. other heavier group 14 hydrides via samarium carbenoids

The relative reactivities of Zn, Al, and Sm carbenoids in the chemoselective carbene insertion reaction of heavier group 14 hydrides were studied. By variation of the reaction protocols using Sm carbenoids, insertion reaction can favour the Ge-H bonds to give Ge-alkylated derivatives in good to high yield.

Formation of silicon-carbon bonds by photochemical irradiation of (η5-C5H5)Fe(CO)2SiR3 and (η5-C5H5)Fe(CO)2Me to Obtain R3SiMe

Photochemical irradiation of an equimolar mixture of (η5 -C5H5)Fe(CO)2SiR3, FpSiR 3, and FpMe leads to the efficient formation of the silicon-carbon-coupled product R3SiMe, R3 = Me 3, Me2Ph, MePh2, Ph3, ClMe 2, Cl2Me, Cl3, Me2Ar (Ar = C 6H4-p-X, X = F, OMe, CF3, NMe2). Similar chemistry occurs with related germyl and stannyl complexes at slower rates, Si > Ge Sn. Substitution of an aryl hydrogen to form FpSiMe2C6H4-p-X has little effect on the rate of the reaction, whereas progressive substitution of methyl groups on silicon by Cl slows the process. Also, changing FpMe to FpCH2SiMe3 dramatically slows the reaction as does the use of (η5-C 5Me5)Fe(CO)2 derivatives. A mechanism involving the initial formation of the 16e intermediate (η5-C 5H5)Fe(CO)Me followed by oxidative addition of the Fe-Si bond accounts for the experimental results obtained.