1665-35-6

Usage

Uses

Used in Organic Synthesis:
2-Phenyl-5-ethylnylthiophene is used as a reactant in the palladium-catalyzed syntheses of naturally occurring acetylenic thiophenes and related compounds. Its ethynyl group allows for efficient coupling reactions with other organic molecules, facilitating the formation of complex molecular structures with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Phenyl-5-ethylnylthiophene is used as a key intermediate in the synthesis of novel therapeutic agents. Its unique structure can be further modified to create new drug candidates with potential applications in treating various diseases and medical conditions.
Used in Material Science:
2-Phenyl-5-ethylnylthiophene is also utilized in material science for the development of new materials with specific properties. Its incorporation into polymers and other materials can lead to the creation of advanced materials with improved electrical, optical, or mechanical properties, which can be applied in various high-tech industries.

InChI:InChI=1/C12H8S/c1-2-11-8-9-12(13-11)10-6-4-3-5-7-10/h1,3-9H

Upstream product

• 1257985-10-6 triisopropyl((5-phenylthiophen-2-yl)ethynyl)silane 
• 5370-19-4 5-iodothiophene-2-carbaldehyde 
• 19163-21-4 5-phenylthiophene-2-carboxaldehyde 
• 558-13-4 carbon tetrabromide 
• 71-43-2 benzene 
• 13781-37-8 2-iodo-5-phenylthiophene 
• 825-55-8 2-phenylthiophene 

Downstream Products

• 94742-70-8 2-phenyl-5-(3-buten-1-ynyl)thiophen 
• 1204-82-6 2-Phenyl-5-(1'-propynyl)-thiophene 

Relevant academic research and scientific papers

Palladium-catalyzed direct alkynylation of thiophenes with halosilylacetylenes

Silylethynylthiophenes were obtained from palladium-catalyzed alkynylation of various thiophenes with 1-halo-2-silylacetylenes. The α-position of thiophenes was alkynylated with high regioselectivity. The terminal silyl groups of products could be replaced by several functional groups.

Photochemical Synthesis of Bithienyl Derivatives

The application of a photochemical arylation of thienyl derivatives to the synthesis of bithienyl compounds is reported.The syntheses of 5-phenyl-2-propynylthiophene and 5-but-3-en-1-ynyl-2,2'-bithienyl are described using as starting materials a phenylthienyl and a bithienyl derivative obtained by this method.Furhtermore, the photochemical synthesis of halogenobithienyl ketones via the photochemical coupling of a halogenothiophene and 2-acetyl-5-iodothiophene is describred.This methodology furnishes a new approach to the synthesis of natural bithienyls.All the synthesized compounds are singlet oxygen photosensitizers, and are, therefore, potentially bioactive compounds.

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).