2,2'-Bithiophene, 4,4'-dioctyl-

Base Information

• Chemical Name: 2,2'-Bithiophene, 4,4'-dioctyl-
• CAS No.: 120762-66-5
• Molecular Formula: C24H38S2
• Molecular Weight: 390.698
• DSSTox Substance ID: DTXSID80470888
• Nikkaji Number: J1.334.451E
• Wikidata: Q82299092
• Mol file: 120762-66-5.mol

Synonyms:2,2'-Bithiophene, 4,4'-dioctyl-;120762-66-5;4,4'-DIOCTYL-2,2'-BITHIOPHENE;4-octyl-2-(4-octylthiophen-2-yl)thiophene;SCHEMBL2012315;DTXSID80470888

Chemical Property of 2,2'-Bithiophene, 4,4'-dioctyl-

Chemical Property:

• XLogP3: 11.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 390.24149356
• Heavy Atom Count: 26
• Complexity: 298

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1=CSC(=C1)C2=CC(=CS2)CCCCCCCC

Technology Process of 2,2'-Bithiophene, 4,4'-dioctyl-

There total 2 articles about 2,2'-Bithiophene, 4,4'-dioctyl- 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: 72.0%

3-octylthiophene (65016-62-8,104934-51-2) → 4,4'-dioctyl-2,2'-bithiophene (120762-66-5)

Guidance literature:

3-octylthiophene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 0 - 50 ℃; for 1h;

With copper dichloride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/pola.24708

Reference yield:

3-octylthiophene (65016-62-8,104934-51-2) + monolithio compound from 3-octylthiophene → 4,4'-dioctyl-2,2'-bithiophene (120762-66-5)

Guidance literature:

DOI:10.1021/j100010a036

Reference yield:

4,4'-dioctyl-2,2'-bithiophene (120762-66-5) → C86H118N4O4S4

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / NBS / CHCl₃; acetic acid / 2 h / 0 °C

2.1: nBuLi; Bu₃SnCl / tetrahydrofuran / 2.67 h / -78 - 20 °C

2.2: 0.18 g / Pd(PPh₃)4 / toluene / 49 h / 20 - 100 °C

3.1: 80 percent / NBS / CHCl₃; acetic acid / 0 °C

4.1: nBuLi; Bu₃SnCl / tetrahydrofuran / 2.67 h / -78 - 20 °C

4.2: 56 mg / Pd(PPh₃)4 / toluene / 49 h / 20 - 100 °C

With N-Bromosuccinimide; n-butyllithium; tributyltin chloride; In tetrahydrofuran; chloroform; acetic acid;

DOI:10.1016/j.tetlet.2006.02.001

upstream raw materials:

3-octylthiophene

Downstream raw materials:

C₆₂H₈₂N₄O₄S₂

C₆₂H₈₁BrN₄O₄S₂

Refernces

• 1、 Zhang, Maojie,Fan, Haijun,Guo, Xia,Yang, Yang,Wang, Shanshan,Zhang, Zhi-Guo,Zhang, Jing,Zhan, Xiaowei,Li, Yongfang. "Synthesis and photovoltaic properties of copolymers based on bithiophene and bithiazole". . p. 2746 - 2754. Retrieved 2011.
• 2、 Hutten, Paul F. van,Gill, Richard E.,Herrema, Jan K.,Hadziioannou, Georges. "Structure of Thiophene-Based Regioregular Polymers and Block Copolymers and Its Influence on Luminescence Spectra". . p. 3218 - 3224. Retrieved 1995.