13737-09-2

Basic information

• Product Name: Pyridine, 5-methyl-2-(trimethylsilyl)- (9CI)
• Synonyms: Pyridine, 5-methyl-2-(trimethylsilyl)- (9CI);5-Methyl-2-(triMethylsilyl)pyridine
• CAS NO: 13737-09-2
• Molecular Formula: C₉H₁₅NSi
• Molecular Weight: 165.3076
• Product Categories: SILYL
• Mol File: 13737-09-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Pyridine, 5-methyl-2-(trimethylsilyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 5-methyl-2-(trimethylsilyl)- (9CI)(13737-09-2)
• EPA Substance Registry System: Pyridine, 5-methyl-2-(trimethylsilyl)- (9CI)(13737-09-2)

Safety Data

• Hazardous Substances Data: 13737-09-2(Hazardous Substances Data)

Upstream product

• 3510-66-5 2-Bromo-5-methylpyridine 
• 75-77-4 chloro-trimethyl-silane 
• 108-99-6 3-Methylpyridine 

Downstream Products

• 139585-59-4 5-Methyl-2-(phenyl-trimethylsilanyloxy-methyl)-pyridine 
• 29681-38-7 methyl 5-methylpyridine-2-carboxylate 

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.

Synthesis and molecular structures of 2-trimethylsilyl-, 2-trimethylgermyl-, and 2-trimethylstannyl-pyridines

5-Methyl-2-trimethylsilyl-pyridine (1) has recently been prepared via the "in situ" Grignard reaction of 1-bromo-5-methyl-pyridine with magnesium and trimethylchlorosilane in refluxing tetrahydrofuran (thf) and structurally characterized. 2-Trimethylgermyl-(2) and 2-trimethylstannyl-pyridine (3) were now obtained from 2-bromo-pyridine through metallation (with n-BuLi) and treatment of the intermediates with Me3GeBr and Me3SnC1, respectively, in diethylether/ thf at -70°C. The crystal and molecular structure of compound 2 has been determined by low temperature (in situ) single crystal X-ray diffraction methods. There is a significant bending of the Me3Ge substituent towards the nitrogen heteroatom [Ge-C-N = 114.7(2)°]. This phenomenon is known from previous studies of the silicon analogue 1 to be not due to intramolecular (peripheral) Si/Ge←N coordination, but to be rather an intrinsic property of the heteroarene skeleton, as also confirmed by quantum-chemical calculations. Furthermore, there is no evidence for intermolecular coordination in the crystals. Such interactions could also be ruled out for the solution state of 2 and 3 through variable temperature multinuclear NMR investigations.