5,5'-Bis(tributylstannyl)-2,2'-bithiophene

Base Information

• Chemical Name: 5,5'-Bis(tributylstannyl)-2,2'-bithiophene
• CAS No.: 171290-94-1
• Molecular Formula: C32H58S2Sn2
• Molecular Weight: 744.365
• European Community (EC) Number: 688-582-8
• DSSTox Substance ID: DTXSID40441296
• Mol file: 171290-94-1.mol

Synonyms:5,5'-bis(tributylstannyl)-2,2'-bithiophene;171290-94-1;Tributyl-[5-(5-tributylstannylthiophen-2-yl)thiophen-2-yl]stannane;AGN-PC-0N63KQ;SCHEMBL1253872;DTXSID40441296;5,5'-Bis(tributylstannyl)-2,2'-bithiophene, 97%

Chemical Property of 5,5'-Bis(tributylstannyl)-2,2'-bithiophene

Chemical Property:

• Boiling Point: 632.7±65.0 °C(Predicted)
• Flash Point: >110℃
• PSA: 0.00000
• Density: 1.217 g/mL at 25 °C
• LogP: 10.61360
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 744.20180
• Heavy Atom Count: 36
• Complexity: 463

Purity/Quality:

98%,99%, ^*data from raw suppliers

5,5′-Bis(tributylstannyl)-2,2′-bithiophene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C1=CC=C(S1)C2=CC=C(S2)[Sn](CCCC)(CCCC)CCCC

Technology Process of 5,5'-Bis(tributylstannyl)-2,2'-bithiophene

There total 2 articles about 5,5'-Bis(tributylstannyl)-2,2'-bithiophene 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: 96.0%

2,2'-Bithiophene (492-97-7) + tributyltin chloride (1461-22-9) → 5,5'-bis(tri-n-butylstannyl)-2,2'-bithiophene (171290-94-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; byproducts: LiCl; n-butyllithium in hexane was added dropwise to a soln. of bithiophene inTHF at -78°C with stirring in N2, the mixt. was warmed to room t emp., stired for 1 h, Sn-compound was added, the mixt. was heated to reflux for 1 h, cooled to room temp.; n-hexane was added, the organic layer was washed with aq. Na2CO3 and water, dried over MgSO4, evapd. in vac.;

DOI:10.1021/ja068964z

Reference yield: 80.0%

tributyltin chloride (1461-22-9) + lithiate-2,2'-bithiophene → 5,5'-bis(tri-n-butylstannyl)-2,2'-bithiophene (171290-94-1)

Guidance literature:

In diethyl ether; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1134/S1070363219090287

Reference yield: 89.0%

5,5'-bis(tri-n-butylstannyl)-2,2'-bithiophene (171290-94-1) + 2-bromo-5-methyl-N,N'-diphenyl-1,4-phenylenediamine (495383-59-0) → C46H38N4S2

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 24h;

DOI:10.1021/ma025833j

upstream raw materials:

2,2'-Bithiophene

tributyltin chloride

Refernces

• 1、 Jousselme, Bruno,Blanchard, Philippe,Levillain, Eric,Delaunay, Jacques,Allain, Magali,Richomme, Pascal,Rondeau, David,Gallego-Planas, Nuria,Roncali, Jean. "Crown-annelated oligothiophenes as model compounds for molecular actuation". . p. 1363 - 1370. Retrieved 2003.
• 2、 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.