2,2'-Bithiophene

Base Information

• Chemical Name: 2,2'-Bithiophene
• CAS No.: 492-97-7
• Molecular Formula: C8H6S2
• Molecular Weight: 166.268
• Hs Code.: 29309090
• European Community (EC) Number: 207-767-2
• UNII: 8CTS9HJ7L6
• DSSTox Substance ID: DTXSID8060084
• Nikkaji Number: J100.273B
• Wikipedia: 2,2%27-Bithiophene,2'-Bithiophene
• Wikidata: Q27116974
• Metabolomics Workbench ID: 55497
• Mol file: 492-97-7.mol

Synonyms:2,2'-Bithiophene;492-97-7;2,2'-Bithienyl;Dithienyl;Bithiophene;2,2'-Dithienyl;2-thiophen-2-ylthiophene;2,2'-Dithiophene;[2,2']Bithiophenyl;2,2-BITHIOPHENE;2-(thiophen-2-yl)thiophene;alpha-bithiophene;MFCD00005414;2-(thien-2-yl)thiophene;8CTS9HJ7L6;C8H6S2;EINECS 207-767-2;2,2 -bithiophene;2,2'-bisthiophene;2,2`-Bithiophene;2,2\'-bithiophene;2,2/'-Bithiophene;2-(2-Thienyl)thiophen;2-thiophen-2-ylthiophen;UNII-8CTS9HJ7L6;SCHEMBL3545;2,2'-Bithiophene, 99%;BIDD:GT0570;DTXSID8060084;CHEBI:36821;OHZAHWOAMVVGEL-UHFFFAOYSA-;BCP16424;BBL100185;GEO-00372;LMFA12000345;STL326750;AKOS005258217;AC-4910;CS-W008787;FD14053;SB66351;DS-15158;SY013839;2,2 inverted exclamation mark -Bithiophene;A7371;AM20100207;B1276;FT-0600879;EN300-117914;W-200391;Q27116974

Chemical Property of 2,2'-Bithiophene

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 32-33 °C(lit.)
• Refractive Index: 1.6210 (estimate)
• Boiling Point: 259.999 °C at 760 mmHg
• Flash Point: 76.261 °C
• PSA: 56.48000
• Density: 1.244 g/cm³
• LogP: 3.47660
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 165.99109254
• Heavy Atom Count: 10
• Complexity: 99.8

Purity/Quality:

99% ^*data from raw suppliers

2,2’-Bithiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=CSC(=C1)C2=CC=CS2
• Description: 2,2'-bithiophene is an intermediate widely used for the synthesis of small molecules or polymer semiconductors in application of organic electronics.?It has proven that?2,2'-bithiophene exists as a mixture of the cis-like and the trans-like planar structures. 5,5'-positions of?2,2'-bithiophene are easily accessible for bromination and stannylation to give 5,5'-dibromo-2,2'-bithiophene or 5,5'-trimethylstannyl-2,2'-bithiophene, which can be used for direct arylation reactions.
• Uses: 2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds. 2,2'-Bithiophene is used as a precursor in the preparation of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene , which is used for the synthesis of small molecules and polymer semiconductors for organic field-effect transistor (OFETs), organic light-emitting diode (OLED), Plastic Light Emitting Diode (PLED) and Organic Photovoltaic (OPV) applications. It is associated with aryl iodides and involved in rhodium catalyzed arylation of heteroarenes. 2,2′-Bithiophene can be polymerized to form poly(2,2′-Bithiophene) which can be electrodeposited on indium tin oxide (ITO) substrates for the fabrication of electrochromic devices. It can also be used in the formation of electrode material for the development of supercapacitors.

Technology Process of 2,2'-Bithiophene

There total 209 articles about 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%

thiophene boronic acid (6165-68-0) → 2,2'-Bithiophene (492-97-7)

Guidance literature:

With sodium carbonate; trans-PdBr(N-Succ)(PPh₃)2; In tetrahydrofuran; at 60 ℃; for 16h;

DOI:10.1021/ol702291r

Reference yield: 99.0%

2-Iodothiophene (3437-95-4,149762-92-5) + thiophene boronic acid (6165-68-0) → 2,2'-Bithiophene (492-97-7)

Guidance literature:

With potassium carbonate; [PS-PEG-adppp-Pd(η³-C3H5)]Cl; In water; at 50 ℃; for 12h;

DOI:10.1021/ol0264298

Reference yield: 99.0%

tributyl(thien-2-yl)stannane (54663-78-4) → 2,2'-Bithiophene (492-97-7)

Guidance literature:

With palladium diacetate; copper dichloride; In tetrahydrofuran; at 23 ℃; for 0.416667h;

DOI:10.1016/S0040-4039(01)01691-4

upstream raw materials:

thiophene

bis(2-thiophenecarbonyl) peroxide

2-bromothiophene

2-Iodothiophene

Downstream raw materials:

2-([2,2']bithienyl-5-carbonyl)-benzoic acid

5,5'-di(1-oxoethyl)-2,2'-bithiophene

2,2'-bithiophene-5-carboxaldehyde

5,5'-diiodo-2,2-bithiophene

Refernces

• 1、 Kilbinger,Feast. "Solution processable alternating oligothiophene-PEO-block-copolymers: Synthesis and evidence for solvent dependent aggregation". . p. 1777 - 1784. Retrieved 2000.
• 2、 Garcia Linares, Guadalupe E.,Nudelman, Norma S.. "Reactions of lithiated aromatic heterocycles with carbon monoxide". . p. 569 - 576. Retrieved 2003.
• 3、 Han, Jianhua,Cheng, ShengLi,Liu, Cheng,Wang, Jinyan,Jian, Xigao. "Influence of donor–acceptor conjugation between thiophene-phthalazinone structures containing Sp3 C?N bond on the frontier orbital levels and optic–electronic properties". . p. 3470 - 3483. Retrieved 2016.
• 4、 Hermet,Bantignies,Rahmani,Sauvajol,Johnson,Serein. "Far- and mid-infrared of crystalline 2,2′-bithiophene: Ab initio analysis and comparison with infrared response". . p. 1684 - 1691. Retrieved 2005.
• 5、 Lukevics, Edmunds,Ryabova, Victoria,Arsenyan, Pavel,Belyakov, Sergey,Popelis, Juris,Pudova, Olga. "Bithienylsilanes: Unexpected structure and reactivity". . p. 8 - 15. Retrieved 2000.
• 6、 Hong, Jin-Hyung,Hwang, Yong-Kyung,Hong, Jin-Yeon,Kim, Hee-Jin,Kim, Sung-Jin,Won, Yong Sun,Huh, Seong. "Facile preparation of SERS-active nanogap-rich Au nanoleaves". . p. 6963 - 6965. Retrieved 2011.
• 7、 -. "SYNTHESIS OF 5-(3-PYRIDYL)-2,2'-BITHIOPHENE(SENSITIZER)". Page/Page column 9. . Retrieved 2021/02/05.
• 8、 Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta. "Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions". . . Retrieved 2021/01/11.