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
Show more names
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
- Formal charge
- 0
- Complexity
- 99.8
Experimental & physicochemical properties
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
- form
- powder to lump to clear liquid
- color
- White or Colorless to Light yellow to Green
- Water Solubility
- Insoluble in water.
- Sensitive
- Light Sensitive
- BRN
- 3039 · 3039
- InChI
- 1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H
- InChIKey
- OHZAHWOAMVVGEL-UHFFFAOYSA-N
- SMILES
- c1csc(c1)-c2cccs2
- LogP
- 3.75 · 3.750
- CAS DataBase Reference
- 492 · 492-97-7(CAS DataBase Reference)
- FDA UNII
- 8 CTS9HJ7L6 · 8CTS9HJ7L6
- EPA Substance Registry System
- 2 · 2,2'-Bithiophene (492-97-7)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- Hazard Codes
- Xi,Xn
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 22 · 22-24/25-36-26
- WGK Germany
- 3 · 3
- F
- 10 · 10-23
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29309090 · 29309090
- Storage Class
- 10 · 10 - Combustible liquids
Safety & regulation
GHS classification
GHS Classification
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
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 22-24/25-36-26
- hazard_class
- IRRITANT
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.
Related reactions
Linked notes
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