2,2′-BITHIOPHENE

2,2′-BITHIOPHENE Basic information
Product Name:2,2′-BITHIOPHENE
Synonyms:2,2′-Bithiophene,98%;2TH;2,2′-Bithiophen;2,2μ-Bithienyl, 2,2μ-Dithienyl;2-(2′-Thieno)thiophene;2,2′-Bithiophene,97%;2,2zzhlxy-Bithiophene;2,2’-dlthienyl
CAS:492-97-7
MF:C8H6S2
MW:166.26
EINECS:207-767-2
Product Categories:pharmacetical;Functional Materials;Thiophenes;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Thiophene Series;Heterocycle-oher series
Mol File:492-97-7.mol
2,2'-BITHIOPHENE Structure
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)
Fp >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
InChIKeyOHZAHWOAMVVGEL-UHFFFAOYSA-N
LogP3.750
CAS DataBase Reference492-97-7(CAS DataBase Reference)
EPA Substance Registry System2,2′-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
10-23
TSCA T
HazardClass IRRITANT
HS Code 29309090
MSDS Information
ProviderLanguage
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
2,2′-BITHIOPHENE Usage And Synthesis
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 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 Propertieswhite to light yellow crystal powder
Uses2,2’Bithiophene is a reactant in the preparation of thienophenyl compounds.
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.
DefinitionChEBI: 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 Description2,2′-Bithiophene is an electron transporting material with the π-electrons present in the system that facilitate charge mobility.
2,2′-BITHIOPHENE Preparation Products And Raw materials
Raw materialsdithiophen-2-ylmercury–>2-(2-THIENYL)PYRIDINE
Preparation Products2,2′-BITHIOPHENE-5-BORONIC ACID–>2,2′-BITHIOPHENE-5-CARBOXALDEHYDE–>2,2′-Bithiophene, 5-(3,5-dibromophenyl)-–>Thiophene(SIV) (9CI)–>4-(2-Ethylhexyl)-4H-dithieno[3,2-b:2′,3′-d]pyrrole–>[2,2’]bithiophenyl-5,5′-dicarbaldehyde–>5-BROMO-2,2′-BITHIOPHENE-5′-CARBOXALDEHYDE–>ALPHA-SEXITHIOPHENE–>O-QUARTERPHENYL–>3,3′-Dibromo-5,5′-bis(trimethylsilyl)-2,2′-bithiophene–>4,4-Dioctyl-4H-silolo[3,2-b:4,5-b’]dithiophene–>2-Thiopheneacetonitrile

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