5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene

Base Information

• Chemical Name: 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene
• CAS No.: 1428332-09-5
• Molecular Formula: C₃₂H₅₆S₂Sn
• Molecular Weight: 623.639
• Mol file: 1428332-09-5.mol

Synonyms:5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene

Chemical Property of 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene

There total 1 articles about 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene 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) → 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene (1428332-09-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2.33 h / -78 °C / Inert atmosphere; Schlenk technique; Large scale

2.2: 1 h / -78 °C / Large scale

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene; 1.1: |Stille Cross Coupling;

DOI:10.1021/ja4057932

Reference yield:

3-hexyl-2-bromothiophene (69249-61-2,125321-66-6) + 5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene (1428332-09-5) → 5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene (154717-19-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 140 ℃; for 0.25h; Microwave irradiation;

DOI:10.1002/chem.201404428

Reference yield:

5-tributylstannyl-3,4’-dihexyl-2,2’-bithiophene (1428332-09-5) → 2-cyano-3-[5’’’-(9-ethyl-9H-carbazol-3-yl)-3’,3’’,3’’’,4-tetrahexyl(2,2’:5’,2’’:5’’,2’’’-quaterthiophene)-5-yl]-2-propenoic acid (1037440-21-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / Reflux

2: trichlorophosphate / 7.5 h / 0 - 70 °C

3: piperidine / toluene; acetonitrile / 4 h / Reflux

With piperidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trichlorophosphate; In toluene; acetonitrile; 1: |Stille Cross Coupling;

DOI:10.1002/chem.201203503

upstream raw materials:

3-hexyl-2-bromothiophene

Downstream raw materials:

2-cyano-3-[5’’’-(9-ethyl-9H-carbazol-3-yl)-3’,3’’,3’’’,4-tetrahexyl(2,2’:5’,2’’:5’’,2’’’-quaterthiophene)-5-yl]-2-propenoic acid

5-(5-(3-hexylthiophen-2-yl)-3-hexylthiophen-2-yl)-3-hexylthiophene

Refernces

• 1、 Hu, Yue,Ivaturi, Aruna,Planells, Miquel,Boldrini, Chiara L.,Biroli, Alessio Orbelli,Robertson, Neil. "'Donor-free' oligo(3-hexylthiophene) dyes for efficient dye-sensitized solar cells". . p. 2509 - 2516. Retrieved 2016/02/20.