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%,99%, ^*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

3’,4’-dinitro-2,2’:5’,2’’-terthiophene

(6R,7R)-8-Oxo-7-phenylacetylamino-3-thiophen-2-ylmethyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

C₂₉H₂₆N₂O₇S

Refernces

• 1、 Konda, Maruthi,Maiti, Sayan,Jadhav, Rohit G.,Das, Apurba K.. "Redox-Active Peptide-Functionalized Quinquethiophene-Based Electrochromic π-Gel". . p. 204 - 209. Retrieved 2018.
• 2、 Cevher, Sevki Can,Unlu, Naime Akbasoglu,Ozelcaglayan, Ali Can,Apaydin, Dogukan Hazar,Udum, Yasemin Arslan,Toppare, Levent,Cirpan, Ali. "Fused structures in the polymer backbone to investigate the photovoltaic and electrochromic properties of donor-acceptor-type conjugated polymers". . p. 1933 - 1941. Retrieved 2013.
• 3、 Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang. "Electrochromic properties of pyrene conductive polymers modified by chemical polymerization". . p. 39291 - 39305. Retrieved 2021/12/27.
• 4、 Cetin, Sultan,Kalay, Erbay,Kolemen, Safacan,Metin, ?nder. "A facile synthesis of mesoporous graphitic carbon nitride supported palladium nanoparticles as highly effective and reusable catalysts for Stille coupling reactions under mild conditions". . p. 6714 - 6723. Retrieved 2020/05/16.