1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-3,3,4,4,5,5-HEXAFLUORO-1-CYCLOPENTENE

Base Information

• Chemical Name: 1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-3,3,4,4,5,5-HEXAFLUORO-1-CYCLOPENTENE
• CAS No.: 137814-07-4
• Molecular Formula: C23H14F6S2
• Molecular Weight: 468.487
• Mol file: 137814-07-4.mol

Synonyms:1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-3,3,4,4,5,5-HEXAFLUORO-1-CYCLOPENTENE;1,2-BIS(2-METHYLBENZO[B]THIOPHENE-3-YL)PERFLUOROCYCLOPENTENE

Chemical Property of 1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-3,3,4,4,5,5-HEXAFLUORO-1-CYCLOPENTENE

Chemical Property:

• Vapor Pressure: 7.24E-10mmHg at 25°C
• Melting Point: 160 °C
• Refractive Index: 1.636
• Boiling Point: 506.1°C at 760 mmHg
• Flash Point: 259.9°C
• PSA: 56.48000
• Density: 1.48g/cm³
• LogP: 8.56310
• Solubility.: slightly sol. in Tetrahydrofuran

Purity/Quality:

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

1,2-Bis[2-methylbenzo[b]thiophen-3-yl]-3,3,4,4,5,5-hexafluoro-1-cyclopentene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-3,3,4,4,5,5-HEXAFLUORO-1-CYCLOPENTENE

There total 8 articles about 1,2-BIS[2-METHYLBENZO[B]THIOPHEN-3-YL]-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: 73.0%

3-bromo-2-methylbenzo[b]thiophene (10243-15-9) + octaperfluorocyclopentene (559-40-0) → 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (137814-07-4)

Guidance literature:

3-bromo-2-methylbenzo[b]thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

octaperfluorocyclopentene; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0036-1588796

Reference yield: 49.0%

octaperfluorocyclopentene (559-40-0) + 3-iodo-2-methylbenzo[b]thiophene (139625-61-9) → 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (137814-07-4)

Guidance literature:

3-iodo-2-methylbenzo[b]thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

octaperfluorocyclopentene; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/poc.2963

Reference yield:

3-bromo-2-methylbenzo[b]thiophene (10243-15-9) + 3-(2-fluoro-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-2-methylbenzo[b]thiophene (152431-65-7) → 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (137814-07-4)

Guidance literature:

3-bromo-2-methylbenzo[b]thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

3-(2-fluoro-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-2-methylbenzo[b]thiophene; In tetrahydrofuran; hexane; at -95 - 20 ℃;

DOI:10.1246/bcsj.76.1625

upstream raw materials:

3-bromo-2-methylbenzo[b]thiophene

octaperfluorocyclopentene

C₂₃H₁₄F₆S₂

3-(2-fluoro-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-2-methylbenzo[b]thiophene

Downstream raw materials:

C₃₇H₂₁F₇N₂OS₄

C₃₂H₁₉F₆NS₃

C₃₇H₂₁F₇N₂O₂S₃

1,2-Bis{6-[4-(1-oxyl-3-oxide-4,4,5,5-tetramethylimidazolin-2-yl)phenyl]-2-methyl-1-benzothiophen-3-yl}hexafluorocyclopentene

Refernces

• 1、 Cheng, Hong-Bo,Huang, Yao-Dong,Zhao, Lina,Li, Xu,Wu, Hai-Chen. "A prominent bathochromic shift effect of indole-containing diarylethene derivatives". . p. 3470 - 3475. Retrieved 2015.
• 2、 Vazquez, Alvaro J.,Nudelman, Norma Sbarbati. "Ring opening/closure reactions of novel diheteroarylethenes derivatives. Solvent effects". . p. 925 - 932. Retrieved 2012.
• 3、 Hanazawa, Makoto,Sumiya, Ritsuo,Horikawa, Yukio,Irie, Masahiro. "Thermally Irreversible Photochromic Systems. Reversible Photocyclization of 1,2-Bis(2-methylbenzothiophen-3-yl)perfluorocycloalkene Derivatives". . p. 206 - 207. Retrieved 1992.
• 4、 Matsuda, Kenji,Irie, Masahiro. "A diarylethene with two nitronyl nitroxides: Photoswitching of intramolecular magnetic interaction". . p. 7195 - 7201. Retrieved 2000.
• 5、 Yamaguchi, Tadatsugu,Irie, Masahiro. "Photochromism of diarylethene derivatives having n-alkylbenzothiophene and n-alkylbenzofuran units". . p. 1100 - 1105. Retrieved 2006.
• 6、 Yamaguchi, Tadatsugu,Irie, Masahiro. "Photochromism of bis(2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene derivatives". . p. 10323 - 10328. Retrieved 2005.
• 7、 Sumi, Takaki,Takagi, Yuta,Yagi, Akira,Morimoto, Masakazu,Irie, Masahiro. "Photoirradiation wavelength dependence of cycloreversion quantum yields of diarylethenes". . p. 3928 - 3930. Retrieved 2014.
• 8、 Tanifuji, Naoki,Matsuda, Kenji,Irie, Masahiro. "Effect of imino nitroxyl and nitronyl nitroxyl groups on the photochromic reactivity of diarylethenes". . p. 3777 - 3780. Retrieved 2005.
• 9、 Bardeen, Christopher J.,Chalek, Kevin,Kitagawa, Daichi,Kobatake, Seiya,Morimoto, Kohei,Mueller, Leonard J.,Tong, Fei. "Correlating Reaction Dynamics and Size Change during the Photomechanical Transformation of 9-Methylanthracene Single Crystals". supporting information. . Retrieved 2021/12/09.
• 10、 Gao, Ting,Li, Hongfeng,Yan, Pengfei,Zhang, Yuan,Zhou, Yanyan. "Metal-directed synthesis of quadruple-stranded helical Eu(iii) molecular switch: A significant improvement in photocyclization quantum yield". supporting information. p. 13213 - 13216. Retrieved 2020/11/09.