Perfluoro-alpha-sexithiophene

Base Information

• Chemical Name: Perfluoro-alpha-sexithiophene
• CAS No.: 347838-21-5
• Molecular Formula: C₂₄F₁₄S₆
• Molecular Weight: 746.638
• DSSTox Substance ID: DTXSID40475733
• Nikkaji Number: J1.541.475H
• Wikidata: Q82306482
• Mol file: 347838-21-5.mol

Synonyms:Perfluoro-alpha-sexithiophene;347838-21-5;2-[3,4-difluoro-5-(3,4,5-trifluorothiophen-2-yl)thiophen-2-yl]-5-[5-[3,4-difluoro-5-(3,4,5-trifluorothiophen-2-yl)thiophen-2-yl]-3,4-difluorothiophen-2-yl]-3,4-difluorothiophene;SCHEMBL13021447;DTXSID40475733;CS-0451473;Perfluoro-2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene;2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-Sexithiophene, 3,3',3'',3''',3'''',3''''',4,4',4'',4''',4'''',4''''',5,5'''''-tetradecafluoro-;2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-Sexithiophene,3,3',3'',3''',3'''',3''''',4,4',4'',4''',4'''',4''''',5,5'''''-tetradecafluoro-

Chemical Property of Perfluoro-alpha-sexithiophene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 286 °C
• Refractive Index: 1.593
• Boiling Point: 555.511°C at 760 mmHg
• Flash Point: 289.763°C
• PSA: 169.44000
• Density: 1.814g/cm³
• LogP: 12.33800
• XLogP3: 10.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 5
• Exact Mass: 745.8100713
• Heavy Atom Count: 44
• Complexity: 964

Purity/Quality:

98% ^*data from raw suppliers

TETRADECAFLUORO-ALPHA-SEXITHIOPHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(=C(SC(=C1F)C2=C(C(=C(S2)C3=C(C(=C(S3)F)F)F)F)F)C4=C(C(=C(S4)C5=C(C(=C(S5)C6=C(C(=C(S6)F)F)F)F)F)F)F)F

Technology Process of Perfluoro-alpha-sexithiophene

There total 4 articles about Perfluoro-alpha-sexithiophene 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: 57.0%

5''-bromo-3,4,5,3',4',3'',4''-heptafluoro-[2,2';5',2'']terthiophene (347838-20-4) → 3,4,5,3',4',3'',4'',3''',4''',3'''',4'''',3''''',4''''',5'''''-tetradecafluoro-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophene (347838-21-5)

Guidance literature:

With copper; In N,N-dimethyl-formamide; at 120 ℃; for 4h;

DOI:10.1021/ja015712j

Reference yield:

5'-bromo-3,4,5,3',4'-pentafluoro-[2,2']bithiophene (347838-18-0) → 3,4,5,3',4',3'',4'',3''',4''',3'''',4'''',3''''',4''''',5'''''-tetradecafluoro-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophene (347838-21-5)

Guidance literature:

Multi-step reaction with 3 steps

1: PdCl₂(PPh₃)2 / dimethylformamide / 3 h / 80 °C

2: 2.67 percent / NBS; acetic acid / 4 h / 80 °C

3: 57 percent / copper bronze / dimethylformamide / 4 h / 120 °C

With N-Bromosuccinimide; copper; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; 1: Stille coupling / 3: Ullmann coupling;

DOI:10.1021/ja015712j

Reference yield:

trimethyl-(3,4,3',4',5'-pentafluoro-[2,2']bithiophen-5-yl)-silane (347838-17-9) → 3,4,5,3',4',3'',4'',3''',4''',3'''',4'''',3''''',4''''',5'''''-tetradecafluoro-[2,2';5',2'';5'',2''';5''',2'''';5'''',2''''']sexithiophene (347838-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 6.41 percent / N-bromosuccinimide; AcOH / 4 h / 80 °C

2: PdCl₂(PPh₃)2 / dimethylformamide / 3 h / 80 °C

3: 2.67 percent / NBS; acetic acid / 4 h / 80 °C

4: 57 percent / copper bronze / dimethylformamide / 4 h / 120 °C

With N-Bromosuccinimide; copper; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; 2: Stille coupling / 4: Ullmann coupling;

DOI:10.1021/ja015712j

upstream raw materials:

5''-bromo-3,4,5,3',4',3'',4''-heptafluoro-[2,2';5',2'']terthiophene

5'-bromo-3,4,5,3',4'-pentafluoro-[2,2']bithiophene

trimethyl-(3,4,3',4',5'-pentafluoro-[2,2']bithiophen-5-yl)-silane

(3,4,3',4',3'',4'',5''-heptafluoro-[2,2';5',2'']terthiophen-5-yl)-trimethyl-silane