17379-37-2

Basic information

• Product Name: Trimethyl(3-pyridyl)silane
• Synonyms: 3-(Trimethylsilyl)pyridine;Trimethyl(3-pyridyl)silane;3-(Trimethylsilyl)pyridin
• CAS NO: 17379-37-2
• Molecular Formula: C₈H₁₃NSi
• Molecular Weight: 151.28
• Mol File: 17379-37-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Trimethyl(3-pyridyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethyl(3-pyridyl)silane(17379-37-2)
• EPA Substance Registry System: Trimethyl(3-pyridyl)silane(17379-37-2)

Safety Data

• Hazardous Substances Data: 17379-37-2(Hazardous Substances Data)

Usage

General Description

Trimethyl(3-pyridyl)silane is a colorless liquid chemical compound with the molecular formula C8H13NSi. It is commonly used as a reagent in organic synthesis, particularly in the formation of silicon-containing compounds. Trimethyl(3-pyridyl)silane is also utilized as a reducing agent in various chemical reactions. Additionally, it is known for its ability to promote the selective reduction of a wide range of functional groups, making it a versatile tool in chemical research and development. Trimethyl(3-pyridyl)silane is highly flammable and should be handled with care in a well-ventilated area.

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

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

Relevant articles and documents

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.

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.

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