104501-58-8

Basic information

• Product Name: 1-Trimethylsilyloxy-1-(3-pyridyl)-ethene
• Synonyms: 1-Trimethylsilyloxy-1-(3-pyridyl)-ethene
• CAS NO: 104501-58-8
• Molecular Formula: C₁₀H₁₅NOSi
• Molecular Weight: 193
• Mol File: 104501-58-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Trimethylsilyloxy-1-(3-pyridyl)-ethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Trimethylsilyloxy-1-(3-pyridyl)-ethene(104501-58-8)
• EPA Substance Registry System: 1-Trimethylsilyloxy-1-(3-pyridyl)-ethene(104501-58-8)

Safety Data

• Hazardous Substances Data: 104501-58-8(Hazardous Substances Data)

Usage

Type of compound

Silane compound

Groups present

Trimethylsilyloxy group and pyridyl group attached to an ethene molecule

Common uses

Reagent in organic synthesis (formation of carbon-carbon and carbon-heteroatom bonds), protective group for alcohols and amines in organic synthesis

Reactions

Addition, elimination, and substitution reactions to introduce functional groups at specific positions on the molecule

Applications

Wide range of applications in organic chemistry

Upstream product

• 350-03-8 methyl-3-pyridylketone 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 36740-10-0 4-oxo-4-(pyridin-3-yl)butanenitrile 
• 6293-82-9 N,N-dimethyl-3-oxo-(3-pyridinyl)-1-propanamine hydrochloride 
• 532-12-7 Myosmine 
• 104501-59-9 3-Hydroxyacetylpyridine 

Relevant articles and documents

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.

Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.

Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2: H -cyclohepta [b] furan-2-ones with silyl enol ethers

We developed a procedure for the direct synthesis of 2-arylazulenes, which were obtained in moderate to excellent yields, by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with aryl-substituted silyl enol ethers. The structures of some 2-arylazulenes were clarified by single-crystal X-ray analysis. The 2-phenylazulene derivatives obtained by this study showed noticeable fluorescence in acidic media.