Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde

Base Information

• Chemical Name: Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde
• CAS No.: 37882-75-0
• Molecular Formula: C8H4O2S2
• Molecular Weight: 196.251
• Hs Code.: 2934999090
• Mol file: 37882-75-0.mol

Synonyms:2,5-diformylthieno[3,2-b]thiophene;2,5-thieno[3,2-b]thiophenedicarbaldehyde;Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde;2,5-Thieno<3,2-b>thiophendicarbaldehyd;

Chemical Property of Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde

Chemical Property:

• Vapor Pressure: 3.14E-06mmHg at 25°C
• Melting Point: 274°C(dec.)(lit.)
• Boiling Point: 388.1oC at 760 mmHg
• Flash Point: 188.5oC
• PSA: 90.62000
• Density: 1.559g/cm3
• LogP: 2.58780
• Storage Temp.: 2-8°C

Purity/Quality:

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

Thieno[3,2-B]thiophene-2,5-dicarbaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37

MSDS Files:

Useful:

• Uses: This molecule has been used in the synthesis of novel metal-free organic dyes for Dye-Sensitized Solar Cells reaching conversion efficiencies of 6.23%.

Technology Process of Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde

There total 7 articles about Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde 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%

thieno[3,2-b]thiophene (251-41-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2,5-Thieno<3,2-b>thiophendicarbaldehyd (37882-75-0)

Guidance literature:

thieno[3,2-b]thiophene; With n-butyllithium; In diethyl ether; hexane; at 0 - 20 ℃; for 2h;

N,N-dimethyl-formamide; In diethyl ether; hexane; at 20 ℃;

Reference yield:

thieno[3,2-b]thiophene (251-41-2) + N-methyl-N-phenylformamide (93-61-8) → 2,5-Thieno<3,2-b>thiophendicarbaldehyd (37882-75-0)

Guidance literature:

thieno[3,2-b]thiophene; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

N-methyl-N-phenylformamide; In tetrahydrofuran; for 2h; Inert atmosphere;

DOI:10.1002/hc.21059

Reference yield:

2,3-dihydro-3-oxothieno<3,2-b>thiophen (82014-59-3) → 2,5-Thieno<3,2-b>thiophendicarbaldehyd (37882-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄ / methanol; CH₂Cl₂ / 3 h / 20 °C

2.1: 0.30 g / aq. HCl / methanol; CH₂Cl₂ / 0.5 h / 20 °C

3.1: n-BuLi / hexane; diethyl ether / 0.25 h / -15 °C

3.2: 50 percent / hexane; diethyl ether / 20 °C

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; In methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1039/b301149f

upstream raw materials:

thieno[3,2-b]thiophene

N,N-dimethyl-formamide

2,3-dihydro-3-oxothieno<3,2-b>thiophen

3-(carboxymethylsulfanyl)thiophene

Downstream raw materials:

2,5-distyrylthieno[3,2-b]thiophene

2,5-bis[p-(butylphenyl)vinyl]-thieno[3,2-b]thiophene

2,5-bis[p-(hexylphenyl)vinyl]-thieno[3,2-b]thiophene

2,5-bis[p-(hexylphenyl)vinyl]-thieno[3,2-b]thiophene

Refernces

• 1、 Xu, Zhiyuan,Lu, Di,Dong, Xiyue,Chen, Mingqian,Fu, Qiang,Liu, Yongsheng. "Highly Efficient and Stable Dion?Jacobson Perovskite Solar Cells Enabled by Extended π-Conjugation of Organic Spacer". . . Retrieved 2021/10/19.
• 2、 Seidler, Arno?t,Svoboda, Ji?í,Dekoj, Václav,Chocholou?ová, Jana Vacek,Vacek, Jaroslav,Stará, Irena G.,Stary, Ivo. "The synthesis of π-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core unit and sulfur alligator clips". supporting information. p. 2795 - 2798. Retrieved 2013/06/05.