5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene

Base Information

• Chemical Name: 5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene
• CAS No.: 850881-10-6
• Molecular Formula: C30H43BrS3
• Molecular Weight: 579.773
• DSSTox Substance ID: DTXSID801229889

Synonyms:5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene;DTXSID801229889;850881-10-6

Chemical Property of 5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene

Chemical Property:

• XLogP3: 14.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 578.17103
• Heavy Atom Count: 34
• Complexity: 529

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCC1=C(SC=C1)C2=CC(=C(S2)C3=CC(=C(S3)Br)CCCCCC)CCCCCC

Technology Process of 5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene

There total 2 articles about 5-Bromo-3',3'',4-trihexyl-2,2':5',2''-terthiophene 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:

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) → 2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (850881-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C

1.2: tri(isopropyl)borate / tetrahydrofuran; hexane / -78 - 20 °C

1.3: tetrahydrofuran; hexane / 20 °C

2.1: 90 percent / aq. NaHCO₃ / [Pd(PPh₃)4] / 1,2-dimethoxy-ethane / 24 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -80 °C

3.2: ZnCl₂ / tetrahydrofuran; hexane / -80 - 20 °C

3.3: 38 percent / [Pd(PPh₃)4] / tetrahydrofuran; hexane / 24 h / 20 °C

With n-butyllithium; sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 3.3: Negishi cross-coupling;

DOI:10.1039/b414817g

Reference yield:

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) → 2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (850881-10-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 90 °C / Inert atmosphere; Schlenk technique; Large scale

2: N-Bromosuccinimide / N,N-dimethyl-formamide; tetrahydrofuran / 2.5 h / -20 - 20 °C / Inert atmosphere; Schlenk technique

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 90 °C / Inert atmosphere; Schlenk technique; Large scale

4: N-Bromosuccinimide / N,N-dimethyl-formamide; tetrahydrofuran / -20 - 20 °C / Inert atmosphere; Schlenk technique; Large scale

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: |Stille Cross Coupling / 3: |Stille Cross Coupling;

DOI:10.1021/ja4057932

Reference yield: 57.0%

2-bromo-5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (850881-10-6) + N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9-phenyl-N-(9-phen-yl-9H-carbazol-3-yl)-9H-carbazol-3-amine → 5''-{4-(N,N-bis[9-phenyl-9H-carbazol-3-yl]phenyl)}-3,4',4''-tri-n-hexyl[2,2',5',2'']terthiophene

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336; sodium carbonate; In toluene; for 48h; Reflux;

DOI:10.5012/bkcs.2013.34.5.1533

upstream raw materials:

3-hexyl-2-bromothiophene

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