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
• General Description: 2,2'-Bithiophene is a key structural unit in organic semiconductors, serving as a central core in quaterthiophene derivatives for p-type semiconductor applications. It can be synthesized via oxidative coupling methods, such as using hypervalent iodine(III) reagents and BF3·Et2O, offering a direct and efficient route without heavy metal catalysts. 2,2'-Bithiophene is valuable for its role in developing conductive and electroluminescent materials, particularly in organic field-effect transistors (OFETs).

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

Quaterthiophenes with terminal Indeno[1,2-b]thiophene units as p-type organic semiconductors

10.1021/jo802028n

The research focuses on the synthesis and characterization of quaterthiophene derivatives, specifically 4T, Oct-4T, and Tol-4T, which are p-type organic semiconductors based on a central 2,2'-bithiophene core with terminal indeno[1,2-b]thiophene units. The study employs Stille and Miyaura-Suzuki couplings for the synthesis, involving reactants such as 2,2'-bithiophenes and derivatives of indeno[1,2-b]thiophene. The electronic properties of these compounds are analyzed through cyclic voltammetry, UV-vis absorption, and fluorescence emission spectroscopy. The thermal stability and solubility of the compounds are also evaluated, and their potential in organic field-effect transistors (OFETs) is explored. The experiments utilize various analytical techniques including mass spectrometry (MALDI-TOF and ESI+ HRMS), nuclear magnetic resonance (NMR), and X-ray diffraction to confirm the structure and purity of the synthesized compounds. The research also details the preparation and characterization of OFETs fabricated from these materials, reporting on their hole-mobility and on/off ratios.

A novel and direct synthesis of alkylated 2,2′-bithiophene derivatives using a combination of hypervalent iodine(III) reagent and BF₃·Et₂O

10.1039/b302462h

The research focuses on the development of a novel and direct synthetic method for alkylated 2,2'-bithiophene derivatives, which are significant precursors for oligo- and poly-thiophenes due to their valuable physical properties like electrical conductivity and electroluminescence. The study presents a nonmetallic oxidative coupling of alkylthiophene derivatives using a combination of hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and boron trifluoride diethyl etherate (BF3·Et2O). The purpose of this research was to find a more direct and efficient route to bithiophenes without the need for transition metal catalyzed coupling reactions, which are typically required for their synthesis. The conclusions drawn from the study indicate that the PIFA-BF3·Et2O system successfully led to the formation of 2,2'-bithiophenes in moderate to good yields, providing a novel and direct route to these important compounds without the need for additional activation of thiophene monomers. This method offers a safer alternative to heavy metal reagents and addresses the challenge of selectively obtaining bithiophenes over polythiophenes, which is a common issue with conventional oxidative methods.

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