58207-97-9

Basic information

• Product Name: Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane
• Synonyms: Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane
• CAS NO: 58207-97-9
• Molecular Formula: C₁₇H₃₈SiSn
• Molecular Weight: 389.27912
• Mol File: 58207-97-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: sol ethers, DMF, hydrocarbon, aromatic solvents.
• CAS DataBase Reference: Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane(CAS DataBase Reference)
• NIST Chemistry Reference: Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane(58207-97-9)
• EPA Substance Registry System: Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane(58207-97-9)

Safety Data

• Hazardous Substances Data: 58207-97-9(Hazardous Substances Data)

Usage

Description

Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane is an organotin compound that features a vinyl group with a trimethylsilyl substituent and a tri-n-butylstannyl group. It is known for its reactivity and utility in various chemical reactions, particularly in the field of organic synthesis.

Uses

Used in Organic Synthesis:
Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane is used as a reagent in the Pd0-catalyzed cross-coupling of vinyl and aryl halides or triflates. This reaction is crucial for the formation of carbon-carbon bonds, which are essential in constructing complex organic molecules and pharmaceuticals.
Used as a Source of β-trimethylsilylvinyllithium:
Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane serves as a precursor for the generation of β-trimethylsilylvinyllithium, a valuable organometallic compound. Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane can be used in various synthetic applications, such as the formation of new carbon-carbon bonds and the functionalization of organic molecules.
Used in Chemical Research:
Due to its unique structure and reactivity, Tributyl[(1E)-2-(trimethylsilyl)ethenyl]stannane is also utilized in chemical research to explore new reaction pathways, develop innovative synthetic methods, and understand the underlying mechanisms of various organic transformations.

Preparation

bis(tri-n-butylstannyl)ethylene is treated successively with molar equivalents of n-butyllithium and chlorotrimethylsilane to give (E)-1-tri-n-butylstannyl-2- trimethylsilylethylene.

Upstream product

• 688-73-3 tri-n-butyl-tin hydride 
• 1066-54-2 trimethylsilylacetylene 
• 4226-01-1 tri-n-butyltin lithium 
• 917-54-4 methyllithium 
• 75-77-4 chloro-trimethyl-silane 
• 74-86-2 acetylene 

Downstream Products

• 72178-87-1 (E)-5-phenyl-1-(trimethylsilyl)pent-1-en-3-ol 
• 159351-39-0 4-(E-1-hydroxy-3-trimethylsilylprop-2-enyl)phenyl acetate 
• 130267-88-8 1-(phenylseleno)-2-(trimethylsilyl)ethene 
• 76999-37-6 2,5,5-Trimethyl-3-((E)-2-trimethylsilanyl-vinyl)-cyclohex-2-enone 
• 159351-38-9 4-(E-1-hydroxy-3-trimethylsilylprop-2-enyl)phenyl-2,2-dimethylpropanoate 
• 130737-55-2 (E)-1-[(S)-1-(Toluene-4-sulfonyl)-pyrrolidin-2-yl]-3-trimethylsilanyl-propenone 
• 119046-50-3 (E)-5-Benzyloxy-1-trimethylsilanyl-pent-1-en-3-ol 
• 125654-43-5 C₃₀H₃₄N₂O₇Si 
• 100514-88-3 C₁₆H₂₃⁽²⁾HSi 
• 174760-55-5 (E)-(3R,4S)-4-(Benzyl-trimethylsilanylmethyl-amino)-1-trimethylsilanyl-pent-1-en-3-ol 
• 70737-22-3 ((E)-2-iodoethenyl)(trimethyl)silane 
• 201947-04-8 N-((E)-(1S,2R)-2-Hydroxy-1-methyl-4-trimethylsilanyl-but-3-enyl)-N-trimethylsilanylmethyl-benzamide 
• 201946-58-9 N-[(E)-(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-4-trimethylsilanyl-but-3-enyl]-N-trimethylsilanylmethyl-benzamide 
• 209529-90-8 N-{2-[4-Hydroxy-2-((E)-2-trimethylsilanyl-vinyl)-phenylsulfanyl]-ethyl}-acetamide 

Relevant articles and documents

ARYLALKYL ESTERS OF 4-AMINO-6-(SUBSTITUTED PHENYL)-PICOLINATES AND 6-AMINO-2-(SUBSTITUTED PHENYL)-PYRIMIDINECARBOXYLATES AND THEIR USE AS SELECTIVE HERBICIDES FOR CROPS

Arylalkyl esters of 4-aminopicolinic acids and 6-amino-4-pyrimidinecarboxylates are herbicides for control of weeds especially those species common to rice and wheat cropping systems and in pasture management programs.

Palladium-Catalyzed Sixfold Alkenylation of Hexabromobenzene: An Interesting Case of Self-Organization

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Stannyl-cupration of Acetylenes and the Reaction of the Intermediate Cuprates with Electrophiles as a Synthesis of Substituted Vinylstannanes

Stannyl-cupration of acetylenes followed by electrophilic attack with a variety of electrophiles gives E-vinylstannanes.These can be used either to form acetylenes, thus achieving overall the addition of an ethynyl group, or to form carbon-carbon bonds in Stille reactions.