2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Base Information

• Chemical Name: 2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• CAS No.: 920504-00-3
• Molecular Formula: C₃₁H₅₄S₂Sn₂
• Molecular Weight: 728.322
• Mol file: 920504-00-3.mol

Synonyms:M7532;CDT-EH-Sn;2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene;(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b]dithiophene-2,6-diyl)bis(trimethylstannane);Stannane, 1,1'-[4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl]bis[1,1,1-trimethyl-

Chemical Property of 2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Chemical Property:

• Boiling Point: Not available
• PSA: 0.00000
• LogP: 10.66000

Purity/Quality:

99.3% ^*data from raw suppliers

(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[1,2-b:5,4-b']dithiophene-2,6-diyl)bis(trimethylstannane) 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: CDT-EH-Sn, namely 4,4-Bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene, is the intermediate for the synthesis of low bandgap semiconducting polymers which are widely used in OLED, OPV and OFET devices.

Technology Process of 2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

There total 7 articles about 2,6-Bis(triMethyltin)-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene 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: 95.0%

4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-20-2) + trimethyltin(IV)chloride (1066-45-1) → 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (920504-00-3)

Guidance literature:

4,4-bis(2-ethylhexyl)-4H-cyclopenta(2,1-b:3,4-b’)-dithiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.333333h;

Reference yield: 59.0%

2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-21-3) + trimethyltin(IV)chloride (1066-45-1) → 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (920504-00-3)

Guidance literature:

2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta(2,1-b:3,4-b’)-dithiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; for 17h; Inert atmosphere;

DOI:10.1039/d0cc00398k

Reference yield:

4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2) → 4,4-bis(2-ethylhexyl)-2,6-bis(trimethylstannyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (920504-00-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide; potassium iodide / dimethyl sulfoxide

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; potassium iodide; potassium hydroxide; In tetrahydrofuran; hexane; dimethyl sulfoxide;

DOI:10.1039/c8tc02863j

upstream raw materials:

4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

trimethyltin(IV)chloride

3-bromomethylheptane

4H-cyclopenta[2,1-b;3,4-b']dithiophene

Refernces

• 1、 Jeong, WonJo,Kang, Jinhyeon,Jeong, Moon-Ki,Won, Jong Ho,Jung, In Hwan. "Development of low bandgap polymers for red and near-infrared fullerene-free organic photodetectors". . p. 10872 - 10879. Retrieved 2021/06/25.
• 2、 Feng, Ru,Sato, Narumi,Yasuda, Takuma,Furuta, Hiroyuki,Shimizu, Soji. "Rational design of pyrrolopyrrole-aza-BODIPY-based acceptor-donor-acceptor triads for organic photovoltaics application". supporting information. p. 2975 - 2978. Retrieved 2020/03/19.