1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene

Base Information

• Chemical Name: 1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene
• CAS No.: 172612-67-8
• Molecular Formula: C29H22 F6 S2
• Molecular Weight: 548.616
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID60443914
• Nikkaji Number: J699.251J
• Wikidata: Q82261901
• Mol file: 172612-67-8.mol

Synonyms:1,2-bis(2,4-dimethyl-5-phenyl-3-thienyl)perfluorocyclopentene

Chemical Property of 1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132 °C
• Refractive Index: 1.605
• Boiling Point: 536.037°C at 760 mmHg
• Flash Point: 277.985°C
• Density: 1.379g/cm³
• XLogP3: 9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 548.10671202
• Heavy Atom Count: 37
• Complexity: 808

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC(=C1C2=C(C(C(C2(F)F)(F)F)(F)F)C3=C(SC(=C3C)C4=CC=CC=C4)C)C)C5=CC=CC=C5
• Uses: 1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene is used in the fabrication and optical characterization of diarylethene nanocrystals for optical applications.

Technology Process of 1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene

There total 11 articles about 1,2-Bis(2,4-dimethyl-5-phenyl-3-thienyl)-3,3,4,4,5,5-hexafluoro-1-cyclopentene 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: 44.0%

octaperfluorocyclopentene (559-40-0) + 2,4-dimethyl-5-phenyl-3-bromothiophene (362513-28-8) → 1,2-bis(2,4-dimethyl-5-phenylthiophen-3-yl)perfluorocyclopentene (172612-67-8)

Guidance literature:

2,4-dimethyl-5-phenyl-3-bromothiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

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

DOI:10.1002/chem.200601316

Reference yield:

2,4-dimethylthiophene (638-00-6) → 1,2-bis(2,4-dimethyl-5-phenylthiophen-3-yl)perfluorocyclopentene (172612-67-8)

Guidance literature:

Multi-step reaction with 3 steps

2: 77 percent / I₂, HIO₃ / CCl₄; acetic acid; H₂O / 2 h / Heating

3: 1) n-BuLi / 1) THF, hexane, 1 h

With n-butyllithium; iodine; iodic acid; In tetrachloromethane; water; acetic acid;

DOI:10.1021/jo00130a035

Reference yield:

iodobenzene (591-50-4) → 1,2-bis(2,4-dimethyl-5-phenylthiophen-3-yl)perfluorocyclopentene (172612-67-8)

Guidance literature:

Multi-step reaction with 3 steps

2: 77 percent / I₂, HIO₃ / CCl₄; acetic acid; H₂O / 2 h / Heating

3: 1) n-BuLi / 1) THF, hexane, 1 h

With n-butyllithium; iodine; iodic acid; In tetrachloromethane; water; acetic acid;

DOI:10.1021/jo00130a035

upstream raw materials:

octaperfluorocyclopentene

3-iodo-2,4-dimethyl-5-phenylthiophene

2,4-dimethyl-5-phenyl-3-bromothiophene

2,4-dimethylthiophene

Refernces

• 1、 Bardeen, Christopher J.,Lansakara, Thiranjeewa I.,Tivanski, Alexei V.,Tong, Fei. "Mechanical Properties and Photomechanical Fatigue of Macro- And Nanodimensional Diarylethene Molecular Crystals". . p. 6744 - 6749. Retrieved 2020.
• 2、 Chiariello, Maria Gabriella,Raucci, Umberto,Coppola, Federico,Rega, Nadia. "Unveiling anharmonic coupling by means of excited state ab initio dynamics: Application to diarylethene photoreactivity". . p. 3606 - 3614. Retrieved 2019.
• 3、 Janssen, René A. J.,Saes, Bart W. H.,Wienk, Martijn M.. "Photochromic organic solar cells based on diarylethenes". . p. 30176 - 30185. Retrieved 2020/10/06.