3,3'-diiodo-2,2'-bithiophene

Base Information

• Chemical Name: 3,3'-diiodo-2,2'-bithiophene
• CAS No.: 90348-22-4
• Molecular Formula: C₈H₄I₂S₂
• Molecular Weight: 418.061
• Mol file: 90348-22-4.mol

Synonyms:3,3’-diiodo-2,2’-bithiophene

Chemical Property of 3,3'-diiodo-2,2'-bithiophene

Chemical Property:

• Melting Point: 145.1-149.5 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 395.9±42.0 °C(Predicted)
• Density: 2.350±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3'-diiodo-2,2'-bithiophene

There total 4 articles about 3,3'-diiodo-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: 70.0%

3,3'dibromo-2,2'-bithiophene (51751-44-1) → 3,3’-diiodo-2,2’-bithiophene (90348-22-4)

Guidance literature:

3,3'dibromo-2,2'-bithiophene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h; Inert atmosphere;

With iodine; In diethyl ether; hexane; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201905734

Reference yield: 45.0%

3,3',5,5'-tetraiodo-2,2'-bithiophene (90007-99-1) → 3,3’-diiodo-2,2’-bithiophene (90348-22-4)

Guidance literature:

With acetic acid; zinc; In methanol; at 0 ℃; for 0.833333h;

DOI:10.1039/c1cc12643a

Reference yield: 36.0%

3-thienyl iodide (10486-61-0) → 3,3’-diiodo-2,2’-bithiophene (90348-22-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 2-methylphenyliodine bis(trifluoroacetate); In dichloromethane; at -78 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.040

upstream raw materials:

3,3'dibromo-2,2'-bithiophene

3-thienyl iodide

3,3',5,5'-tetraiodo-2,2'-bithiophene

Downstream raw materials:

4-(4H-dithieno[3,2-b:2',3'-d]pyrrol-4-yl)benzaldehyde

Refernces

• 1、 Watanabe, Hiroyuki,Kumagai, Jun,Tsurugi, Hayato,Satoh, Tetsuya,Miura, Masahiro. "Synthesis of alkylated benzo[2,1-b:3,4-6′]dithiophenes by annulative coupling and their direct arylation under palladium catalysis". . p. 1336 - 1337. Retrieved 2007.
• 2、 Harschneck, Tobias,Zhou, Nanjia,Manley, Eric F.,Lou, Sylvia J.,Yu, Xinge,Butler, Melanie R.,Timalsina, Amod,Turrisi, Riccardo,Ratner, Mark A.,Chen, Lin X.,Chang, Robert P. H.,Facchetti, Antonio,Marks, Tobin J.. "Substantial photovoltaic response and morphology tuning in benzo[1,2-b:6,5-b′]dithiophene (bBDT) molecular donors". supporting information. p. 4099 - 4101. Retrieved 2014/04/03.