5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene

Base Information

• Chemical Name: 5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene
• CAS No.: 153561-79-6
• Molecular Formula: C₄₀H₅₈S₄
• Molecular Weight: 667.165
• DSSTox Substance ID: DTXSID701215045
• Nikkaji Number: J1.686.730F
• Mol file: 153561-79-6.mol

Synonyms:153561-79-6;5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene;2-Dodecyl-5-[5-[5-(5-dodecylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene;DTXSID701215045;2,2':5',2'':5'',2'''-Quaterthiophene, 5,5'''-didodecyl-;MFCD30475652;D4889;D90348

Chemical Property of 5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene

Chemical Property:

• Melting Point: 166°C(lit.)
• XLogP3: 17.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 25
• Exact Mass: 666.34213654
• Heavy Atom Count: 44
• Complexity: 641

Purity/Quality:

97% ^*data from raw suppliers

5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene >96.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCC1=CC=C(S1)C2=CC=C(S2)C3=CC=C(S3)C4=CC=C(S4)CCCCCCCCCCCC

Technology Process of 5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene

There total 6 articles about 5,5'''-Didodecyl-2,2':5',2'':5'',2'''-quaterthiophene 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%

5,5'-dibromo-2,2'-bisthiophene (4805-22-5) + C16H27BrMgS (916910-68-4) → 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene (153561-79-6)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; for 64h; Heating;

DOI:10.1055/s-1993-26009

Reference yield:

2-dodecylthiophene (4861-61-4) + 5,5'-dibromo-2,2'-bisthiophene (4805-22-5) + trimethyltin(IV)chloride (1066-45-1) → 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene (153561-79-6)

Guidance literature:

2-dodecylthiophene; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 30h;

trimethyltin(IV)chloride; In tetrahydrofuran; for 3h;

5,5'-dibromo-2,2'-bisthiophene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 18h; Further stages.; Heating;

DOI:10.1002/ejoc.200700566

Reference yield:

2-dodecylthiophene (4861-61-4) → 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene (153561-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / NBS / dimethylformamide / 4 h / Ambient temperature

2: Mg / diethyl ether / Heating

3: 70 percent / Ni(dppp)Cl₂ / diethyl ether / 64 h / Heating

With N-Bromosuccinimide; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); magnesium; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1055/s-1993-26009

upstream raw materials:

5,5'-dibromo-2,2'-bisthiophene

C₁₆H₂₇BrMgS

2-dodecylthiophene

2,2'-Bithiophene