13737-10-5

Usage

Uses

Used in Organic Synthesis:
2-Methyl-6-(triMethylsilyl)pyridine is used as a base for facilitating various reactions, such as the deprotonation of acidic compounds, which is essential for the synthesis of numerous organic molecules. Its ability to stabilize carbanions and its reactivity in forming carbon-silicon bonds make it a versatile component in the creation of complex organic structures.
Used in Organometallic Chemistry:
In organometallic chemistry, 2-Methyl-6-(triMethylsilyl)pyridine serves as a ligand, capable of forming stable complexes with metal ions. This role is crucial for the development of catalysts and the study of metal coordination environments, contributing to advances in homogeneous catalysis and materials science.
Used in Coordination Chemistry:
As a ligand in coordination chemistry, 2-Methyl-6-(triMethylsilyl)pyridine is employed to create complexes that can have specific properties, such as luminescence or magnetic behavior. Its use in this field aids in the design of new materials with tailored characteristics for applications in sensors, pharmaceuticals, and other areas.

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 1282608-35-8 C₅H₃N(Si(CH₃)3)CHCCH₃NHC₆H₃(CH(CH₃)2)2 
• 13602-11-4 6-methylpicolinic acid methyl ester 

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.

6,6′-Dimethyl-2,2′-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands

We describe an efficient and scalable synthesis of 4-carbomethoxy-6,6′-dimethyl-2,2′-bipyridine starting from easily available substituted 2-halopyridines and based on the application of modified Negishi cross-coupling conditions. This compound is a versatile starting material for the synthesis of 4-functionalized 2,2′-bipyridines bearing halide, alcohol, amine, and other functionalities, suitable for conjugation to biological material (2a-c, 3a-g). The utility of this compound in the construction of more complex architectures was further demonstrated by the synthesis of two bifunctional lanthanide chelators; an open chain ligand based on one 2,2′-bipyridine unit and a cryptand based on three 2,2′-bipyridine units [N2(bpy)3COOMe]. In the field of luminophoric biolabels, the photophysical properties of the corresponding Eu(III) cryptate are reported.

Preparation of Tricarbonyl(η6-pyridine)chromium(0) Complexes

The synthesis of tricarbonyl(η6-pyridine)chromium(0) complexes is accomplished via complexation of 2-silylpyridines with subsequent fluoride ion-mediated desilylation under mild conditions.The tricarbonylchromium(0) complexes of pyridine, 2-methylpyridine, 3-methylpyridine, 2-ethylpyridine, 2-(but-3-enyl)pyridine and 2-(6-trimethylsilylpyridyl)-1,3-dioxolane are prepared.Deprotonation (lithium diisopropylamide) and methylation (methyl iodide) of tricarbonyl(η6-pyridine)chromium(0) converts it cleanly to tricarbonyl(η6-2-methylpyridine)chromium(0).