2-(Tributylstannyl)thiophene

Base Information

• Chemical Name: 2-(Tributylstannyl)thiophene
• CAS No.: 54663-78-4
• Molecular Formula: C16H30 S Sn
• Molecular Weight: 373.19
• Hs Code.: 2934999090
• European Community (EC) Number: 640-336-0
• DSSTox Substance ID: DTXSID80381420
• Mol file: 54663-78-4.mol

Synonyms:tri-n-butyl(2-thienyl)stannane

Chemical Property of 2-(Tributylstannyl)thiophene

Chemical Property:

• Vapor Pressure: 2.95E-05mmHg at 25°C
• Melting Point: 197-198 °C
• Refractive Index: n20/D 1.518(lit.)
• Boiling Point: 155 °C0.1 mm Hg(lit.)
• Flash Point: 221 °F
• PSA: 28.24000
• Density: 1.175 g/mL at 25 °C(lit.)
• LogP: 5.80420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 374.109025
• Heavy Atom Count: 18
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

2-(Tributylstannyl)thiophene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C1=CC=CS1
• Uses: 2-(Tri-n-butylstannyl)thiophene derivative is employed in Stille reaction involving efficient carbon-carbon bond formation. 2-(Tributylstannyl)thiophene has been used to synthesize diphenylquinoxaline monomer for the electrochromism polymers. It can also be used as a reactant in Stille coupling reaction.

Technology Process of 2-(Tributylstannyl)thiophene

There total 10 articles about 2-(Tributylstannyl)thiophene 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: 100.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) + tributyltin chloride (1461-22-9) → tributyl(thien-2-yl)stannane (54663-78-4)

Guidance literature:

thiophene; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

tributyltin chloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.cclet.2010.12.054

Reference yield: 95.0%

2-Iodothiophene (3437-95-4,149762-92-5) + bis(tri-n-butyltin) (813-19-4) → tributyltin iodide (7342-47-4) + tributyl(thien-2-yl)stannane (54663-78-4)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In N,N,N,N,N,N-hexamethylphosphoric triamide; 20°C, molar ratio distannane/halide 2:1, 80 min;

DOI:10.1007/BF01141722

Reference yield: 92.0%

→ tributyl(thien-2-yl)stannane (54663-78-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 27h; Inert atmosphere;

upstream raw materials:

2-Iodothiophene

bis(tri-n-butyltin)

tributyltin chloride

thiophene

Downstream raw materials:

2,2'-Bithiophene

2,2':5',2''-terthiophene

2,2'-bithiophene-5-carboxaldehyde

4-thiophen-2-yl-phenol

Refernces

Molecular engineering of organic dyes containing N-aryl carbazole moiety for solar cell

10.1016/j.tet.2006.12.082

The research focuses on the molecular engineering of organic dyes containing the N-aryl carbazole moiety for application in solar cells, specifically dye-sensitized solar cells (DSSCs). The purpose of this study was to design and synthesize novel organic dyes that could overcome the limitations of low conversion efficiency and operational stability often associated with organic dyes in DSSCs, as compared to metal-based complexes. The researchers aimed to develop alternative, highly efficient organic dyes that could potentially rival the performance of ruthenium complexes, which are known for their high efficiency but are prohibitively expensive. In the process, various chemicals were used, including 2-iodo-9,9-dimethylfluorene, 3-iodocarbazole, 1-bromo-4-(2,2-diphenylvinyl)benzene, and (2-thienylmethyl)triphenylphosphonium bromide, which were synthesized using modified procedures from previous references. Other chemicals involved in the synthesis steps included tributyl(thiophen-2-yl)stannane, Pd(PPh3)4, copper bronze, potassium carbonate, 18-crown-6, n-butyl lithium, cyanoacetic acid, piperidine, rhodanine-3-acetic acid, and ammonium acetate, among others. These chemicals were utilized in a series of reactions such as coupling, lithiation, and condensation to synthesize the target dyes, which were then tested for their photovoltaic performance in DSSCs.

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