243468-48-6

Basic information

• Product Name: 2,2'-[METHYLENEBIS(DIMETHYLSILYLENE)]BISPYRIDINE
• Synonyms: 2,2'-[METHYLENEBIS(DIMETHYLSILYLENE)]BISPYRIDINE;METHYLENEBIS[DIMETHYL(2-PYRIDYL)SILANE];BIS[DIMETHYL(2-PYRIDYL)SILYL]METHANE;Bis[dimethyl(2-pyridyl)silyl]methane 2,2'-[Methylenebis(dimethylsilylene)]bispyridine
• CAS NO: 243468-48-6
• Molecular Formula: C₁₅H₂₂N₂Si₂
• Molecular Weight: 286.52
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 243468-48-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 358.5±27.0 °C(Predicted)
• Appearance: /
• Density: 0.99±0.1 g/cm3(Predicted)
• PKA: 6.16±0.12(Predicted)
• CAS DataBase Reference: 2,2'-[METHYLENEBIS(DIMETHYLSILYLENE)]BISPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-[METHYLENEBIS(DIMETHYLSILYLENE)]BISPYRIDINE(243468-48-6)
• EPA Substance Registry System: 2,2'-[METHYLENEBIS(DIMETHYLSILYLENE)]BISPYRIDINE(243468-48-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 243468-48-6(Hazardous Substances Data)

Usage

General Description

2,2'-[Methylenebis(dimethylsilylene)]bispyridine is a chemical compound with the molecular formula C20H24N2Si2. It is a silane-based compound that is commonly used as a catalyst for various organic reactions, particularly in the production of silicone polymers. This chemical is known for its ability to facilitate the formation of silicon-carbon bonds and is often utilized in the synthesis of organosilicon compounds. Its unique structure, consisting of two pyridine rings connected by a central silicon atom, makes it a valuable tool in the field of organometallic chemistry and materials science. Additionally, 2,2'-[Methylenebis(dimethylsilylene)]bispyridine exhibits potential for use in the development of new functional materials and pharmaceuticals.

Upstream product

• 21032-48-4 2-(dimethylhydrosilyl)pyridine 
• 13737-04-7 2-(trimethylsilyl)pyridine 

Downstream Products

• 270588-98-2 (E)-2-pyridyldimethyl[2-(2,4,6-trimethylphenyl)ethenyl]silane 
• 270588-99-3 (E,E)-bis{1,4-[2-(2-pyridyldimethylsilyl)ethenyl]}benzene 
• 350846-54-7 (E,E)-2-pyridyldimethyl(4-phenylbuta-1,3-dienyl)silane 
• 270588-96-0 (E)-β-dimethyl(2-pyridyl)silyl-styrene 
• 270589-02-1 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene 

Relevant articles and documents

Pyridyl group assisted deprotonation of a methyl group on silicon: Complex induced proximity effect and novel hydroxymethylation

A novel methodology for the deprotonation of a methyl group on silicon has been developed. This newly developed α-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the α-silyl carbanion together with the inherent silicon α effect. It was found that the deprotonation (t-BuLi/Et2O/-78 °C) occurs with 2-pyridyltrimethylsilane but not with other related silanes such as phenyltrimethylsilane, 3-pyridyltrimethylsilane, and 4-pyridyltrimethylsilane. It seems that this deprotonation proceeded through the agency of the complex-induced proximity effect (CIPE) of a 2-pyridyl group on silicon. 1H NMR analysis of (2-pyridyldimethylsilyl)methyllithium revealed the intramolecular coordination of a pyridyl group to lithium. (2-Pyridyldimethylsilyl)-methyllithium was found to react with chlorosilanes, hydrosilanes, chlorostannanes, bromine, iodine, organic bromides, aldehydes, and ketones in good to excellent yields. The resultant adducts were further oxidized with H2O2/KF to give the corresponding alcohols in excellent yields. Thus, this two-step transformation provides an efficient method for the nucleophilic hydroxymethylation.

[Bis(2-pyridyldimethylsilyl)methyl]lithium. New reagent for the stereoselective synthesis of vinylsilanes

(formula presented) The generation of (2-PyMe2Si)2CHLi was easily accomplished by the deprotonation of (2-PyMe2Si)2CH2 using n-BuLi in Et2O. Thus generated (2-PyMe2Si)2/sub