Tributyl(vinyl)tin

Base Information

• Chemical Name: Tributyl(vinyl)tin
• CAS No.: 7486-35-3
• Molecular Formula: C14H30Sn
• Molecular Weight: 317.102
• Hs Code.: 29312000
• European Community (EC) Number: 231-291-4
• UNII: 2FA6XM467X
• DSSTox Substance ID: DTXSID40225836
• Wikipedia: Vinyl_tributyltin
• Wikidata: Q72510158
• Mol file: 7486-35-3.mol

Synonyms:ethynyltributylstannane;ethynyltributyltin

Chemical Property of Tributyl(vinyl)tin

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 0.0156mmHg at 25°C
• Melting Point: <0 °C
• Refractive Index: n20/D 1.478(lit.)
• Boiling Point: 104-106 °C (3.5 mmHg)
• Flash Point: 43 °C
• PSA: 0.00000
• Density: 1.085 g/mL at 25 °C(lit.)
• LogP: 5.56070
• Storage Temp.: Refrigerator
• Water Solubility.: Not miscible or difficult to mix in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 318.136954
• Heavy Atom Count: 15
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

Tributyl(vinyl)tin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53-10
• Safety Statements: 35-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C=C
• Uses: Tributyl(vinyl)tin is used as a reagent in the palladium catalyzed synthesis of allyl and benzyl ethers. Tributyl(vinyl)tin is also a vinyl nucleophile for bromoacetylene and bromoaromatics. Tributyl(vinyl)tin is used as a reagent in the palladium catalyzed synthesis of allyl and benzyl ethers. It is also a vinyl nucleophile for bromoacetylene and bromoaromatics.

Technology Process of Tributyl(vinyl)tin

There total 21 articles about Tributyl(vinyl)tin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Bu3Sn(Me)CuCNLi2 + acetylene (74-86-2,25067-58-7) → tri-n-butyl(vinyl)tin (7486-35-3)

Guidance literature:

With ammonium chloride; In not given; -78°C to 0°C, NH4Cl;

DOI:10.1039/c39920000351

Reference yield: 99.0%

tri-n-butyltin lithium (4226-01-1) + methyllithium (917-54-4) + copper(l) cyanide + acetylene (74-86-2,25067-58-7) → tri-n-butyl(vinyl)tin (7486-35-3)

Guidance literature:

In tetrahydrofuran; a soln. of tributylstannyllithium in THF and MeLi in hexane and CuCN is stirred at -78°C for 30 min; addn. of acetylene; reaction mixt. warmed to 0°C, addn. of satd. aq. NH4Cl; extn. (Et2O), drying (MgSO4), chromy.;

Reference yield: 97.0%

2Li(1+)*(C6H5)(CH3)2Si(Sn(C4H9)3)Cu(1-)*CN(1-) = (C6H5)(CH3)2Si(Sn(C4H9)3)CuLi*LiCN + acetylene (74-86-2,25067-58-7) → tri-n-butyl(vinyl)tin (7486-35-3)

Guidance literature:

In tetrahydrofuran; substrate added to the Cu compound at -78°C, mixt. allowed to warm to room temp.; aq. work-up; extd. (diethyl ether), chromd. (SiO2, hexane);

upstream raw materials:

tributyltin chloride

vinyllithium

vinyl magnesium bromide

vinylmagnesium chloride

Downstream raw materials:

tributyltin chloride

tributyltin bromide

2-methyl-3-buten-2-ol

tributylphenylstannane

Refernces

ATTACHMENT OF THE ANTHRAMYCIN ACRYLAMIDE SIDE CHAIN BY THE PALLADIUM CATALYZED COUPLING REACTION OF A VINYL TRFLATE

10.1016/S0040-4039(00)96916-8

The research focuses on the attachment of the anthramycin acrylamide side chain to the pyrrolo(1,4)benzodiazepine structure via a palladium-catalyzed coupling reaction of a vinyl triflate. Anthramycin, an antitumor antibiotic, has a complex synthesis process. The study explores a more efficient route by converting the 2-keto group in the pyrrolo ring to a vinyl triflate and then coupling it with various reagents. Key chemicals involved include N-methyl isatoic anhydride, L-hydroxyproline, triflic anhydride, pyridine, tributylvinylstannane, ethyl acrylate, and palladium catalysts such as (Ph3P)2Pd and PdCl2. The methodology provides a convenient procedure for constructing anthramycin derivatives, offering a rapid entry into the pyrrolo(1,4)benzodiazepine structure with the desired side chain.

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