(5-(1,3-Dioxolan-2-yl)thiophen-2-yl)tributylstannane

Base Information

• Chemical Name: (5-(1,3-Dioxolan-2-yl)thiophen-2-yl)tributylstannane
• CAS No.: 349616-56-4
• Molecular Formula: C19H34O2SSn
• Molecular Weight: 445.254
• DSSTox Substance ID: DTXSID90579331
• Mol file: 349616-56-4.mol

Synonyms:(5-(1,3-dioxolan-2-yl)thiophen-2-yl)tributylstannane;349616-56-4;tributyl-[5-(1,3-dioxolan-2-yl)thiophen-2-yl]stannane;[5-(1,3-Dioxolan-2-yl)thiophen-2-yl]tributylstannane;SCHEMBL972409;DTXSID90579331;LPAWLMVOUBWAHW-UHFFFAOYSA-N;Tributyl[5-(1,3-dioxolan-2-yl)thiophen-2-yl]stannane

Chemical Property of (5-(1,3-Dioxolan-2-yl)thiophen-2-yl)tributylstannane

Chemical Property:

• Boiling Point: 452.1±55.0 °C(Predicted)
• PSA: 46.70000
• LogP: 5.53930
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 446.130154
• Heavy Atom Count: 23
• Complexity: 299

Purity/Quality:

98%Min ^*data from raw suppliers

(5-(1,3-DIOXOLAN-2-YL)THIOPHEN-2-YL)TRIBUTYLSTANNANE 95.00% ^*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)C2OCCO2

Technology Process of (5-(1,3-Dioxolan-2-yl)thiophen-2-yl)tributylstannane

There total 3 articles about (5-(1,3-Dioxolan-2-yl)thiophen-2-yl)tributylstannane 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: 75.0%

2-(5-bromothiophen-2-yl)-1,3-dioxolane (52157-62-7) + tributyltin chloride (1461-22-9) → 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)thiophene (349616-56-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; (protected from light and O2); BuLi/THF added at-78°C under N2 to2-bromo-5-dioxolanylthiophene/THF, stirred for 1 h at -78°C, Sn compd. added, reacted for 1 h 30 min; H2O and Et2O added, the org. layer extd. (H2O and satd. soln. of NH4Cl),the org. phase dried (MgSO4), evapd. (vac.), distd.;

DOI:10.1016/S0022-328X(00)00833-0

Reference yield: 42.0%

2-(2-thienyl)-1,3-dioxolane (58268-08-9) + tributyltin chloride (1461-22-9) → Tributyl [5-(1.3-dioxolan-2-yl)-2-thienyllstannane + 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)thiophene (349616-56-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane;

Reference yield: 34.0%

2-(2-thienyl)-1,3-dioxolane (58268-08-9) + tributyltin chloride (1461-22-9) → 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)thiophene (349616-56-4)

Guidance literature:

2-(2-thienyl)-1,3-dioxolane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h; Inert atmosphere;

tributyltin chloride; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 16.25h; Inert atmosphere;

DOI:10.1002/chem.201404843

upstream raw materials:

2-(2-thienyl)-1,3-dioxolane

tributyltin chloride

2-(5-bromothiophen-2-yl)-1,3-dioxolane

Downstream raw materials:

5-(4-(9-butyl-9H-pyreno[4,5-d]imidazol-10-yl)phenyl)thiophene-2-carbaldehyde

5-(8-(diphenylamino)-6,6,12,12-tetrakis(2-ethylhexyl)-6,12-dihydroindeno[1,2-b]fluoren-2-yl)thiophene-2-carbaldehyde

4,4'-(5'-(4-(diphenylamino)phenyl)-2-thiophene-4,5-diyl)dithiophenaldehyde

(2E,2’E)-3,3’-(4,4’-(5’-(4-(diphenylamino)phenyl)-2-thiophene-4,5-diyl)bis(4,1-thiophenylene))bis(2-cyanoacrylic acid)

Refernces

• 1、 Krause, André,Hertl, Alexander,Muttach, Fabian,J?schke, Andres. "Phosphine-Free Stille-Migita Chemistry for the Mild and Orthogonal Modification of DNA and RNA". supporting information. p. 16613 - 16619. Retrieved 2016/02/12.
• 2、 -. "ORGANIC SEMICONDUCTOR MATERIAL". Page/Page column 31; 32. . Retrieved 2014/06/11.