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Merck
CN

241636

2,2′-Bithiophene

99%

Synonym(s):

2,2′-Bithienyl, 2,2′-Dithienyl

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About This Item

Empirical Formula (Hill Notation):
C8H6S2
CAS Number:
492-97-7
Molecular Weight:
166.26
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
24854316
EC Number:
207-767-2
Beilstein/REAXYS Number:
3039
MDL number:
MFCD00005414

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Product Name

2,2′-Bithiophene, 99%

InChI key

OHZAHWOAMVVGEL-UHFFFAOYSA-N

InChI

1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H

SMILES string

c1csc(c1)-c2cccs2

assay

99%

bp

260 °C (lit.)

mp

32-33 °C (lit.)

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Application

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.
Substrate used in a rhodium-catalyzed C-H arylation of heteroarenes with aryl iodides.

General description

2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1442
STBJ6281
STBG5849V
STBG4222V
STBF5730V

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Electrode material dependent p-or n-like thermoelectric behavior of single electrochemically synthesized poly (2, 2?-bithiophene) layer?application to thin film thermoelectric generator.
Kublitski J, et al.
Journal of Solid State Electrochemistry, 20(8), 2191-2196 (2016)
Shuichi Yanagisawa et al.
Journal of the American Chemical Society, 128(36), 11748-11749 (2006-09-07)
A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO){P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides
Electrochemical characterization of the Poly (2, 2'-Bithiophene-co-Pyrene) Functionalized Single-Walled Carbon Nanotubes Films and Their Applications in Supercapacitors Field.
Baibarac M, et al.
International Journal of Electrochemical Science, 12(3), 2013-2025 (2017)
Applications of Poly (indole-6-carboxylic acid-co-2, 2?-bithiophene) Films in High-Contrast Electrochromic Devices.
Kuo C, et al.
Coatings, 8(3), 102-102 (2018)
5, 5 `-Bis (dimesitylboryl)-2, 2 `-bithiophene and 5, 5 ``-bis (dimesitylboryl)-2, 2 `: 5 `, 2 ``-terthiophene as a novel family of electron-transporting amorphous molecular materials.
Noda T and Shirota Y
Journal of the American Chemical Society, 120(37), 9714-9715 (1998)
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