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HomeProduct name list2,2'-BITHIOPHENE

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
2,2'-BITHIOPHENE Structural

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)
ghs
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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