4805-21-4

Basic information

• Product Name: 2,2'-Bithiophene, 5-(phenylethynyl)-
• CAS NO: 4805-21-4
• Molecular Formula: C16H10S2
• Molecular Weight: 266.387
• Mol File: 4805-21-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,2'-Bithiophene, 5-(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bithiophene, 5-(phenylethynyl)-(4805-21-4)
• EPA Substance Registry System: 2,2'-Bithiophene, 5-(phenylethynyl)-(4805-21-4)

Safety Data

• Hazardous Substances Data: 4805-21-4(Hazardous Substances Data)

Usage

Chemical composition

Consists of a 2,2'-bithiophene core with a phenylethynyl group attached at the 5-position.

Type of compound

Heterocyclic compound containing a five-membered ring of two sulfur atoms and three carbon atoms.

Usage

Commonly used in the field of organic electronics for its ability to function as a conductive and luminescent material.

Applications

Utilized in the synthesis of organic semiconductors and as a building block in the production of polymers and materials for applications in optoelectronics and photovoltaics.

Potential applications

Has potential applications in the development of organic light-emitting diodes and organic photovoltaic devices due to its electronic and optical properties.

Upstream product

• 492-97-7 2,2'-Bithiophene 
• 536-74-3 phenylacetylene 
• 3480-11-3 5-bromo(2,2'-bithiophene) 
• 250643-76-6 tris((2-phenyl)ethynyl)indium 
• 3339-79-5 5-iodo-2,2'-bithiophene 

Relevant articles and documents

Palladium-catalyzed oxidative cross-coupling between heterocycles and terminal alkynes with low catalyst loading

Direct: With [Pd2(dba)3] as a catalyst, the direct alkynylation of thiophenes bearing a variety of substituents has been accomplished by using terminal alkynes as alkynylating reagents. This protocol is also applicable to other electron-rich aromatic heterocycles. dba=dibenzylidenacetone. Copyright

PALLADIUM-CATALYZED SYNTHESES OF NATURALLY-OCCURRING ACETYLENIC THIOPHENS AND RELATED COMPOUNDS

5-(3-buten-1-ynyl)-2,2'-bithienyl (1a), a natural product first isolated from Tagetes roots which shows nematicidal and photo-induced fungicidal activity, and 2-phenyl-5-(3-buten-1-ynyl) thiophen (1b) have been synthesized using two different methods.The first one (Method A) involves the palladium-catalyzed cross-coupling of vinyl bromide with the Grignard reagents derived from 5-ethynyl-2,2'-bithienyl (6a) and 2-ethynyl-5-phenylthiophen (6b).The second method (Method B) utilizes the coupling reaction of vinyl bromide with 6a and 6b, respectively, in the presence of a catalytic amount of (PPh3)4Pd and CuI.Such reaction, which was carried out under phase-transfer conditions employing BnEt3N(+)Cl(-) as phase transfer agent and 2.5N aq NaOH as base, has been also employed to prepare a large number of heterocyclic acetylene derivatives including some naturally-occuring compounds.The experimental conditions of Method B allow also the direct production of heterocyclic acetylene derivatives (1) starting from 1-alkynyltrimethylsilanes (5) and organic halides (2).