19752-27-3

Usage

Uses

Used in Organic Synthesis:
Tributyl(2-phenylethenyl)stannane is used as a reagent in organic synthesis for the formation of carbon-carbon bonds. Its unique properties allow it to facilitate complex chemical reactions, making it a valuable component in the creation of various organic compounds.
Used in the Stille Coupling Reaction:
In the field of organic chemistry, Tributyl(2-phenylethenyl)stannane is utilized as a reagent in the Stille coupling reaction, which is a cross-coupling reaction between an organotin compound and an organic halide to form new carbon-carbon bonds. This reaction is crucial for the synthesis of complex organic molecules, including pharmaceuticals and natural products.
Used in Polymer Production:
Tributyl(2-phenylethenyl)stannane is also employed in the production of polymers, where it contributes to the formation of specific polymer structures. Its use in this industry is indicative of its versatility and the breadth of its applications in material science.
Used as a Stabilizer in PVC Plastics:
In the plastics industry, Tributyl(2-phenylethenyl)stannane serves as a stabilizer in PVC (polyvinyl chloride) plastics. It helps to prevent the degradation of PVC, thereby extending the lifespan and improving the performance of the final plastic products.
While the provided materials do not specify different applications across various industries, the uses listed above cover the primary functions of Tributyl(2-phenylethenyl)stannane in organic synthesis, chemical reactions, polymer production, and the plastics industry. Its multifaceted role underscores its importance in the realm of chemical manufacturing and material science.

Upstream product

• 1461-22-9 tributyltin chloride 
• 2687-12-9 cinnamyl chloride 
• 51800-74-9 1-phenylallyl magnesium chloride 
• 2327-99-3 1-phenylpropadiene 
• 1426-65-9 1,2,2-trifluorovinyl tri-n-butylstannane 
• 36635-36-6 3-butenyltributylstannane 
• 100-42-5 styrene 
• 66222-29-5 tri-n-butylstannylmethyl iodide 
• 17955-46-3 trimethylsilyltributyltin 
• 77821-95-5 3-phenyl-2-propen-1-yl 2,2-dimethylproponate 
• 104-54-1 3-Phenylpropenol 
• 24850-33-7 allyltributylstanane 
• 68725-14-4 tri-n-butyltin triflate 
• 74785-32-3 (E)-cinnamyl(tributyl)tin 

Downstream Products

• 768-03-6 Phenyl vinyl ketone 
• 462093-17-0 1,3,4-triphenylhex-5-en-1-one 
• 57082-95-8 2,2-Dichloro-3-phenyl-pent-4-enal 
• 32121-04-3 N-cinnamyl-4-methylbenzenesulfonamide 
• 58567-43-4 4-methyl-N-(1-phenyl-allyl)-benzenesulfonamide 
• 1067-97-6 tributyltin hydroxide 
• 1187159-11-0 C₂₂H₂₁N 
• 40596-15-4 3-phenyl-1-hexene-4-ol 
• 54985-35-2 (E)-1-Phenylhex-1-en-4-ol 
• 54985-34-1 trans-1-phenyl-1-penten-3-ol 

Relevant academic research and scientific papers

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.

Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage

A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.

Addition of allylstannanes to an oxy-stabilized carbenium ion on a 1,7-dioxaspiro[5.5]undecane ring system

The nucleophilic addition of allylstannanes to (2R*,5S*,6S*)-2-acetoxy-5-benzyloxy-1,7-dioxaspiro-[5.5] undecane 1 has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78°C. In the exa

Photochemical 1,3-stannyl rearrangement of allylic stannanes

The photochemical 1,3-stannyl rearrangement of allylic stannanes has been investigated. The photorearrangement of (E)-cinnamyl(triphenyl)stannane is not observed in benzene under anaerobic conditions, while the photoinduced 1,3-stannyl migration takes place in the same solvent under aerobic conditions, or in the presence of organic halides or a radical-trapping agent to give a photoequllibrium mixture of the cinnamylstannane and its branched regioisomer, 1-phenylprop-2-enyl(triphenyl)stannane, with the latter predominating. Cinnamyl(trialkyl)stannanes and their homologues also afford the corresponding branched allylstannanes under similar photochemical conditions. These 1,3-stannyl migrations proceed intramolecularly via cinnamyl π-π* excitation in competition with homolytic (cinnamyl)C-Sn bond fission. In contrast, the 1,3-stannyl migration of crotyl- and prenyl-(tributyl)-stannanes is not efficient, but their triphenyl or dibutylphenyl derivatives undergo the 1,3-rearrangement via excitation of the phenyl group(s) on the tin atom to give a regioisomeric mixture of the starting linear tin compounds and the branched ones with the former predominating.

The Synthesis of Allylstannanes and Vinylstannanes by the Stannyl-cupration of Allenes

Stannyl-cupration of allenes followed by electrophilic attack gives allyl- and vinylstannanes with a variety of substitution patterns; the regiochemistry of the reaction depends upon the temperature and the nature of the stannyl-cuprate reagent.