2,2'-BITHIOPHENE
Synonym(s):2,2′-Bithienyl;2,2′-Dithienyl
- CAS NO.:492-97-7
- Empirical Formula: C8H6S2
- Molecular Weight: 166.26
- MDL number: MFCD00005414
- EINECS: 207-767-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-11 17:04:31
What is 2,2'-BITHIOPHENE?
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.
Chemical properties
white to light yellow crystal powder
The Uses of 2,2'-BITHIOPHENE
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.
The Uses of 2,2'-BITHIOPHENE
2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds.
The Uses of 2,2'-BITHIOPHENE
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.
Definition
ChEBI: A thiophene derivative that consists of two thiophene rings connected by a 2,2'-linkage.
Synthesis Reference(s)
The Journal of Organic Chemistry, 51, p. 2627, 1986 DOI: 10.1021/jo00364a002
Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983
General Description
2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.
Properties of 2,2'-BITHIOPHENE
Melting point: | 32-33 °C (lit.) |
Boiling point: | 260 °C (lit.) |
Density | 1.2455 (rough estimate) |
refractive index | 1.6210 (estimate) |
Flash point: | >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 |
CAS DataBase Reference | 492-97-7(CAS DataBase Reference) |
EPA Substance Registry System | 2,2'-Bithiophene (492-97-7) |
Safety information for 2,2'-BITHIOPHENE
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2,2'-BITHIOPHENE
InChIKey | OHZAHWOAMVVGEL-UHFFFAOYSA-N |
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