1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene

Base Information

• Chemical Name: 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene
• CAS No.: 182003-69-6
• Molecular Formula: C₂₇H₁₈F₆S₂
• Molecular Weight: 520.562
• DSSTox Substance ID: DTXSID001026764
• Nikkaji Number: J782.111E
• Mol file: 182003-69-6.mol

Synonyms:1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene;182003-69-6;3,3'-(Perfluorocyclopent-1-ene-1,2-diyl)bis(2-methyl-5-phenylthiophene);SCHEMBL423920;OUCKAFOKXHCQPT-UHFFFAOYSA-N;DTXSID001026764

Chemical Property of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene

Chemical Property:

• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 520.07541189
• Heavy Atom Count: 35
• Complexity: 751

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=C(S1)C2=CC=CC=C2)C3=C(C(C(C3(F)F)(F)F)(F)F)C4=C(SC(=C4)C5=CC=CC=C5)C

Technology Process of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene

There total 20 articles about 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene 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: 95.0%

3-(3,3,4,4,5,5-hexafluoro-2-(5-iodo-2-methylthiophen-3-yl)cyclopent-1-enyl)-5-iodo-2-methylthiophene + phenylboronic acid (98-80-6) → 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl(3-thienyl))cyclopent-1-enyl)-2-methyl-5-phenylthiophene (182003-69-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; for 2h; Reflux;

DOI:10.1002/chem.201301645

Reference yield: 81.0%

3-bromo-2-methyl-5-phenylthiophene (61285-25-4) + octaperfluorocyclopentene (559-40-0) → 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl(3-thienyl))cyclopent-1-enyl)-2-methyl-5-phenylthiophene (182003-69-6)

Guidance literature:

3-bromo-2-methyl-5-phenylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

octaperfluorocyclopentene; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Further stages.;

DOI:10.1021/ja993181h

Reference yield: 75.0%

3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene) (159590-16-6) + phenylboronic acid (98-80-6) → 3-(3,3,4,4,5,5-hexafluoro-2-(2-methyl-5-phenyl(3-thienyl))cyclopent-1-enyl)-2-methyl-5-phenylthiophene (182003-69-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; for 3h; Reflux;

DOI:10.1002/chem.201301645

upstream raw materials:

3-bromo-2-methyl-5-phenylthiophene

octaperfluorocyclopentene

bromobenzene

1,2-bis(5'-dibutoxyboryl-2'-methylthien-3'-yl)perfluorocyclopentene

Downstream raw materials:

(C₅F₆(C₄H(C₆H₅)(CH₃)S)(C₄H(CH₃)S(C₆H₅)RuCl₂))2

1-(1,1-dioxo-2-methyl-5-phenyl-3-thienyl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene