17379-37-2

Usage

Uses

Used in Organic Synthesis:
Trimethyl(3-pyridyl)silane is used as a reagent for the formation of silicon-containing compounds, which are important in various chemical and pharmaceutical applications.
Used in Chemical Reactions:
Trimethyl(3-pyridyl)silane is used as a reducing agent to facilitate various chemical reactions, enhancing the efficiency and selectivity of the processes.
Used in Chemical Research and Development:
Trimethyl(3-pyridyl)silane is utilized for its ability to promote selective reduction of a wide range of functional groups, making it a valuable tool in advancing chemical research and development.
Used in Pharmaceutical Industry:
Trimethyl(3-pyridyl)silane may be used as a reagent in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Material Science:
In the field of material science, Trimethyl(3-pyridyl)silane can be employed in the synthesis of silicon-containing materials with unique properties, such as improved thermal stability or enhanced electrical conductivity.
Used in Environmental Applications:
Trimethyl(3-pyridyl)silane may also be used in environmental applications, such as the reduction of pollutants or the synthesis of environmentally friendly materials.

Upstream product

• 110-86-1 pyridine 
• 75-77-4 chloro-trimethyl-silane 
• 626-55-1 3-Bromopyridine 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Downstream Products

• 5424-19-1 3-Benzoylpyridine 
• 139585-63-0 3-(Phenyl-trimethylsilanyloxy-methyl)-pyridine 
• 1096622-73-9 4',7-diacetoxy-2-(pyridin-3-yl)-isoflav-3-ene 

Relevant academic research and scientific papers

CO2 Conversion into Esters by Fluoride-Mediated Carboxylation of Organosilanes and Halide Derivatives

A one-step conversion of CO2 into heteroaromatic esters is presented under metal-free conditions. Using fluoride anions as promoters for the C-Si bond activation, pyridyl, furanyl, and thienyl organosilanes are successfully carboxylated with CO2 in the presence of an electrophile. The mechanism of this unprecedented reaction has been elucidated based on experimental and computational results, which show a unique catalytic influence of CO2 in the C-Si bond activation of pyridylsilanes. The methodology is applied to 18 different esters, and it has enabled the incorporation of CO2 into a polyester material for the first time. Metal free! A novel methodology is described to convert CO2 into heteroaromatic esters in the presence of organosilanes and organic halides using fluoride anions as promoters for the C-Si bond activation (see scheme). CO2 exhibits a unique catalytic influence in the C-Si bond cleavage of pyridylsilanes, serving as a traceless activator.

Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems

A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.

Unusual t-BuLi induced ortholithiation versus halogen-lithium exchange in bromopyridines: Two alternative strategies for functionalization

The reaction of lithiating agents with various 3-bromopyridines has been investigated. An unprecedented selectivity was observed with t-BuLi, which effected a clean lithiation at C-4. With 3-bromo and 2-chloro-3-bromo pyridines, the ortholithiation-exchange ratio was strongly electrophile and addition order dependent while 2-chloro-5-bromopyridine always gave exclusive C-4 substitution.

Synthese d'aryl- et heteroarylsilanes par scission de l'hexamethyldisilane

In the presence of hexamethylphosphormaide and a catalytic quantity of tetrakis(triphenylphosphine)palladium, hexamethyldisilane reacts with various functional aryl bromides to give the corresponding arylsilanes in satisfactory yields.The reaction has bee

On the Mechanism of the Carbodesilylation of 4- or 5-Substituted 2-(Trimethylsilyl)pyridines

An "ylide mechanism" is proposed for the carbodesilylation of 2-(trimethylsilyl)pyridines with benzaldehyde.In contrast, 3- and 4-(trimethylsilyl)pyridines, react only in the presence of a base catalyst via pyridyl anions with electrophiles.The rates of the uncatalyzed carbodesilylation reactions of 4-substituted 2-(trimethylsilyl)pyridines 2 with benzaldehyde correlate very well with the resonance parameters of the substituents ?0R, whereas the rates of 5-substituted 2-(trimethylsilyl)pyridines 7 correlate with the inductive substituent parameters ?1 in the Taft equation.This is to our knowledge the first direct determination of the resonance parameters ?0R.Key Words: Pyridines, substituted 2-(trimethylsilyl)-, synthesis of, carbodesilylation of / Carbodesilylation / Rate constants

Synthesis and 1H, 13C, 14N, 15N, 29Si NMR study of trimethylsilylquinolines and their methiodides

2-, 3-, 4-, 5-, 6-, 7-, and 8-trimethylsilylquinolines and their methiodides as well as some 2-silylalkylquinolines were obtained by lithium synthesis in order to elucidate intramolecular donor-acceptor interactions between nitrogen and silicon atoms. 1H, 13C, 14N, 15N and 29Si NMR spectra of the compounds were studied and quantum-chemical calculation of charges on individual atoms in the unsubstituted quinoline and in trimethylsilylquinoline molecule was carried out.The two-centred component of the total system energy for various bonds was calculated.The findings suggest donor-acceptor interaction between nitrogen and silicon atoms in 2-trimethylsilylquinoline that reduces electron density at nitrogen atoms.An apparently weaker interaction is observed in 8-trimethylsilylquinoline.

Electrochemical Synthesis of Organosilicon Compounds

Electrochemical reduction of allyl, aryl, and vinyl halides in the presence of a silylating agent (Me3SiCl, HMe2SiCl, and PhMe2SiCl) in a solution of tetraethylammonium tosylate in dimethylformamide (DMF) gave the corresponding organosilicon compounds.The regioselectivity of the reaction of allylic halides depends on the nature of the silylating agent.Trimethylsilyl and dimethylphenylsilyl groups were introduced to the less substituted end of the allyl group, whereas the dimethylsilyl group was introduced to both ends of the allyl group.High chemoselectivity of the present approach was demonstrated by selectivity monosilylations of p-bromoiodobenzene and p-bromocinnamyl chloride to obtain (p-bromophenyl)trimethylsilane and (p-bromocinnamyl)trimethylsilane, respectively.A mechanism involving a carbanion intermediate is suggested.

ELECTROCHEMICAL SYNTHESIS OF ORGANOSILICON COMPOUNDS

Electrochemical reduction of allyl, vinyl, and aryl halides in the presence of a silylating agent (Me3SiCl, HMe2SiCl, or PhMe2SiCl) afforded the corresponding organosilicon compounds offering a valuable method for introduction of a silyl group into organic molecules.

Functionalization of Pyridine via Direct Metallation

The isolation of mixtures of 2-, 3-, and 4-deuteriopyridine, 2-, 3-, and 4-trimethylsilylpyridine, or 2-, 3-, and 4-methylthiopyridine indicates successful metallation of pyridine with a 1:1 mixture of BuLi-ButOK in tetrahydrofuran-hexane at -100 deg C.