2,2'-BITHIOPHENE Chemical Properties

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

InChIKey

OHZAHWOAMVVGEL-UHFFFAOYSA-N

LogP

3.750

CAS DataBase Reference

492-97-7(CAS DataBase Reference)

EPA Substance Registry System

2,2'-Bithiophene (492-97-7)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

F 

10-23

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,2'-BITHIOPHENE Usage And Synthesis

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

Uses

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

Uses

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.

Uses

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.

2,2'-BITHIOPHENE(492-97-7)Related Product Information

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