2,6-Di3MeTin-4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene

Base Information

• Chemical Name: 2,6-Di3MeTin-4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene
• CAS No.: 920515-35-1
• Molecular Formula: C₃₇H₆₀B₂O₄S₂
• Molecular Weight: 654.635
• Mol file: 920515-35-1.mol

Synonyms:2,6-Di3MeTin-4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene;4H-Cyclopenta[2,1-b:3,4-b']dithiophene, 4,4-bis(2-ethylhexyl)-2,6-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 2,6-Di3MeTin-4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene

Chemical Property:

• PSA: 50.60000
• LogP: 12.25300

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,6-Di3MeTin-4,4-di(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b]dithiophene

There total 9 articles about 2,6-Di3MeTin-4,4-di(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: 91.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-20-2) → 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene (920515-35-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; to soln. dthiophene in THF at -78°C n-BuLi in hexane was added dropwise, stirred at -78°C for 1 h, warmed to room temp., stirred for 2 h, cooled to -78°C, 1,3,2-dioxaborolane was added, warmed toroom temp., stirred overnight; react. mixt. was poured into water and extd. with hexane, dried over MgSO4, solvent was removed in vacuo, residue was dried in vacuo for 24 h;

DOI:10.1021/ja208917m

Reference yield: 51.3%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene (365547-21-3) → 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene (920515-35-1)

Guidance literature:

In tetrahydrofuran; at -80 - 20 ℃; Inert atmosphere;

DOI:10.1002/pola.25933

Reference yield:

4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2) → 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4-di(2-ethylhexyl)-4H-cyclopenta-[2,1-b:3,4-b']dithiophene (920515-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium iodide; potassium hydroxide / dimethyl sulfoxide / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

2.2: -78 - 20 °C

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

DOI:10.1021/ja208917m

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

3-thiophene carboxaldehyde

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

Refernces

• 1、 Lange, Alexander,Krueger, Hartmut,Ecker, Bernhard,Tunc, Ali Veysel,Von Hauff, Elizabeth,Morana, Mauro. "Influence of different copolymer sequences in low band gap polymers on their performance in organic solar cells". . p. 1622 - 1635. Retrieved 2012/06/01.