Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-

Base Information

• Chemical Name: Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-
• CAS No.: 222730-43-0
• Molecular Formula: C15H8Cl2F6S2
• Molecular Weight: 437.257
• Mol file: 222730-43-0.mol

Synonyms:

Chemical Property of Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl-

There total 1 articles about Thiophene, 3,3'-(3,3,4,4,5,5-hexafluoro-1-cyclopentene-1,2-diyl)bis[5-chloro-2-meth yl- 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:

2-chloro-5-methylthiophene (17249-82-0) → 1,2-bis(5-chloro-2-methylthien-3-yl)perfluorocyclopent-1-ene (222730-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / bromine / CHCl₃ / 2 h / 0 - 20 °C

2: 70 percent / nBuLi / diethyl ether; hexane / 0.75 h / -78 °C

3: 55 percent / Zn dust; TiCl₃*3THF / tetrahydrofuran / 1 h / 40 °C

With n-butyllithium; titanium trichloride tris(tetrahydrofuran); bromine; zinc; In tetrahydrofuran; diethyl ether; hexane; chloroform; 3: McMurry coupling;

DOI:10.1002/1099-0690(200301)2003:1<155::AID-EJOC155>3.0.CO;2-S

Reference yield: 94.0%

4-carboxyphenylboronic acid (14047-29-1) + 1,2-bis(5-chloro-2-methylthien-3-yl)perfluorocyclopent-1-ene (222730-43-0) → 1,2-bis(2-methyl-5-(4-carboxyphenyl)thiophen-3-yl)hexafluorocyclopentene (243971-25-7)

Guidance literature:

4-carboxyphenylboronic acid; 1,2-bis(5-chloro-2-methylthien-3-yl)perfluorocyclopent-1-ene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; water; Inert atmosphere; Reflux;

With hydrogenchloride; In 1,2-dimethoxyethane; water;

DOI:10.1016/j.tetlet.2009.01.102

Reference yield: 86.0%

p-hydroxymethylphenylboronic acid (59016-93-2) + 1,2-bis(5-chloro-2-methylthien-3-yl)perfluorocyclopent-1-ene (222730-43-0) → 1,2-bis[2-methyl-5-(p-(hydroxymethyl)phenyl)-3-thienyl]hexafluorocyclopentene (210093-64-4)

Guidance literature:

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

DOI:10.1016/j.tetlet.2009.01.102

upstream raw materials:

2-chloro-5-methylthiophene

Downstream raw materials:

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

3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-bromo-2-methylthiophene)

1,2-bis[2-methyl-5-(p-(hydroxymethyl)phenyl)-3-thienyl]hexafluorocyclopentene

1,2-bis(2-methyl-5-(4-carboxyphenyl)thiophen-3-yl)hexafluorocyclopentene

Refernces

• 1、 Lucas, Linda N.,De Jong, Jaap J. D.,Van Esch, Jan H.,Kellogg, Richard M.,Feringa, Ben L.. "Syntheses of dithienylcyclopentene optical molecular switches". . p. 155 - 166. Retrieved 2007/10/03.