2,2'-Bithiophene

HCID 68120CAS 492-97-7

Basic information

Standard SMILES
c1csc(-c2cccs2)c1
InChIKey
OHZAHWOAMVVGEL-UHFFFAOYSA-N
Molecular formula
C8H6S2
Average molar mass
166.3 g/mol
Monoisotopic mass
165.99109219

Overview

2,2'-bithiophene is a thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.

Names & identifiers

Preferred name
2,2'-Bithiophene
IUPAC
2-thiophen-2-ylthiophene
English name
2,2'-BITHIOPHENE
Molecular formula
C8H6S2
Molecular weight
166.26

Names & synonyms

2,2'-Bithiophene492-97-72,2'-BithienylDithienyl2-thiophen-2-ylthiophene2,2'-Dithienyl2,2'-Dithiophene2-(thiophen-2-yl)thiophenealpha-bithiophene2-(thien-2-yl)thiophene8CTS9HJ7L62,2'-bisthiophene
Show more names
2T2THS10202,2-DITHIENYL2,2’-dlthienyl2,2'-Bithiophen
EINECS 207-767-2DTXSID8060084CHEBI:36821OHZAHWOAMVVGEL-UHFFFAOYSA-2,2'DithienylRefChem:80696DTXCID0040678207-767-2

Database identifiers

CAS
492-97-7
PubChem CID
68120
DTXSID
DTXSID8060084
ChEBI
CHEBI:36821
UNII
8CTS9HJ7L6
EC Number
207-767-2
Nikkaji
J100.273B

Properties

Computed structural properties

XLogP
3
Topological polar surface area
56.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Thiophenes
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SpringerMaterials PropertiesSchoenflies notation
LogP3.75
Vapor Pressure0.00119 [mmHg]
Physical DescriptionMelting point = 33 deg C; [ChemIDplus] Clear yellow to liquid; mp = 32-34 deg C; [Aldrich MSDS]

Physicochemical properties

Melting point
32 · 32-33 °C (lit.)
Boiling point
260 °C · 260 °C (lit.)
Density
1.2455 · 1.2455 (rough estimate)
refractive index
1.621 · 1.6210 (estimate)
Flash point
230 °F · >230 °F
storage temp.
Keep in dark place,Inert atmosphere,Room temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 14.3% (1 of 7) of reports.

Warning

H302 (14.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 7 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryMay cause irritation; Not considered a dangerous material by the Globally Harmonized System (GHS); [Aldrich MSDS] See Thiophene.
Hazard Classes and CategoriesAcute Tox. 4 (14.3%)

Safety data

F
10-23
PPE
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk
3
tsca
TSCA listed
hs_code
29309090
risk_code
20/21/22-36/37/38

Chemistry & industry

Uses & manufacturing

General Manufacturing Information2,2'-Bithiophene: ACTIVE
Applications · 5 items

Description2,2'-bithiophene is an intermediate widely used for the synthesis of small molecules or polymer semiconductors in application of organic electronics.It has proven that2,2'-bithiophene exists as a mixture of the cis-like and the trans-like planar structures. 5,5'-positions of2,2'-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.

Uses2,2'-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.

Uses2,2′-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.

Uses2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds.

General Description2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]

Additional notes

DefinitionChEBI: A thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.

Related reactions

68 records

Linked notes

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