3,3',5,5'-Tetrabromo-2,2'-bithiophene

Base Information

• Chemical Name: 3,3',5,5'-Tetrabromo-2,2'-bithiophene
• CAS No.: 125143-53-5
• Molecular Formula: C8H2Br4S2
• Molecular Weight: 481.852
• Hs Code.: 2934999090
• European Community (EC) Number: 663-436-6
• DSSTox Substance ID: DTXSID50372380
• Nikkaji Number: J389.656K
• Wikidata: Q63409723
• Mol file: 125143-53-5.mol

Synonyms:3,3',5,5'-Tetrabromo-2,2'-bithiophene;125143-53-5;3,5-dibromo-2-(3,5-dibromothiophen-2-yl)thiophene;2,2'-Bithiophene, 3,3',5,5'-tetrabromo-;SCHEMBL2015363;AMY7187;DTXSID50372380;MOMHMPZSZNZLAK-UHFFFAOYSA-N;BCP11157;GEO-02780;MFCD00114807;AKOS015835496;CCG-252859;CS-W004537;AC-27930;DS-17466;FT-0718192;T2699;3,3',5,5'-Tetrabromo-2,2'-bithiophene, 97%;3,3'5,5'-TETRABROMO-2,2'-BITHIOPHENE;A852737;W-200096;Q63409723

Chemical Property of 3,3',5,5'-Tetrabromo-2,2'-bithiophene

Chemical Property:

• Melting Point: 138.0 to 144.0 °C
• Boiling Point: 371 °C at 760 mmHg
• Flash Point: 178.2 °C
• PSA: 56.48000
• Density: 2.428g/cm³
• LogP: 6.52660
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 481.62904
• Heavy Atom Count: 14
• Complexity: 194

Purity/Quality:

98% ^*data from raw suppliers

3,5-Dibromo-2-(3,5-dibromothiophen-2-yl)thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(SC(=C1Br)C2=C(C=C(S2)Br)Br)Br
• Uses: suzuki reaction

Technology Process of 3,3',5,5'-Tetrabromo-2,2'-bithiophene

There total 8 articles about 3,3',5,5'-Tetrabromo-2,2'-bithiophene 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: 100.0%

2,2'-Bithiophene (492-97-7) → 3,3',5,5'-tetrabromo-2,2'-bithiophene (125143-53-5)

Guidance literature:

With N-Bromosuccinimide;

DOI:10.1021/ja00078a090

Reference yield: 95.0%

3-bromo-[2,2’]bithiophenyl (19690-69-8) → 3,3',5,5'-tetrabromo-2,2'-bithiophene (125143-53-5)

Guidance literature:

With N-Bromosuccinimide; acetic acid; In chloroform; at 20 - 50 ℃; for 20h;

DOI:10.1021/ol402420w

Reference yield: 90.0%

5,5'-dibromo-2,2'-bisthiophene (4805-22-5) → 3,3',5,5'-tetrabromo-2,2'-bithiophene (125143-53-5)

Guidance literature:

With N-Bromosuccinimide; In chloroform; acetic acid; for 72h; Heating;

DOI:10.1246/bcsj.62.1539

upstream raw materials:

3,3'dibromo-2,2'-bithiophene

2,2'-Bithiophene

5,5'-dibromo-2,2'-bisthiophene

3,5-dibromo-[2]thienyl lithium

Downstream raw materials:

2,2’-bis[4-(diphenylamino)phenyl]-6,6’-diformyl-4,4’-spirobi[cyclopenta[2,1-b;3,4-b’]dithiophene]

2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophen-4-one

4H-cyclopenta[2,1-b:3,4-b']dithiophen-4-one

2,6-bis-(tert-butyl-dimethyl-silanyl)-4-phenyl-4H-phospholo[3,2-b;4,5-b']dithiophene

Refernces

• 1、 Jiu, Tonggang,Liu, Huibiao,Fu, Liming,He, Xiaorong,Wang, Ning,Li, Yuliang,Ai, Xicheng,Zhu, Daoben. "Novel blue-light-emitting hybrid materials based on oligothiophene acids and ZnO". . p. 113 - 117. Retrieved 2004.
• 2、 Li, Fanchao,Hu, Zhiwei,Qiao, Hongbing,Liu, Lin,Hu, Jiawei,Chen, Xuegang,Li, Jie. "Terpyridine-based donor-acceptor metallo-supramolecular polymers with tunable band gaps: Synthesis and characterization". . p. 142 - 150. Retrieved 2016.
• 3、 Okamoto, Tsuyoshi,Kakinami, Takaaki,Fujimoto, Hiroshi,Kajigaeshi, Shoji. "Halogenation Using Quaternary Ammonium Polyhalides. XXXI. Halogenation of Thiophene Derivatives with Benzyltrimethylammonium Polyhalides". . p. 2566 - 2568. Retrieved 1991.
• 4、 Algethami, Norah,Ferri, Nicolò,Higgins, Simon J.,Lambert, Colin J.,McLaughlin, Maeve,Nichols, Richard J.,Sadeghi, Hatef,Sangtarash, Sara,Vezzoli, Andrea. "Hemilabile Ligands as Mechanosensitive Electrode Contacts for Molecular Electronics". . p. 16583 - 16589. Retrieved 2019.
• 5、 Tereniak, Stephen J.,Bruns, David L.,Stahl, Shannon S.. "Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst". . p. 20318 - 20323. Retrieved 2020.
• 6、 Khor, Eugene,Ng, Siu Choon,Li, Hwee, Chze,Chai, Selenium. "SELECTIVE FUNCTIONALIZATION OF 2,2'-BITHIOPHENES". . p. 1805 - 1812. Retrieved 1991.
• 7、 Li, Ming,Liu, Zhao,Sun, Yuanhui,Xu, Yanmin,Yan, Lihe,Yang, Xiaolong,Yue, Ling,Zhou, Guijiang. "Iridium(iii) complexes with the dithieno[3,2-: B:2′,3′- d] phosphole oxide group and their high optical power limiting performances". supporting information. p. 4967 - 4976. Retrieved 2020/04/24.
• 8、 -. "Preparation method of thiophene organic semiconductor material intermediate". Paragraph 0036; 0038-0045. . Retrieved 2020/01/08.