4805-17-8

Basic information

• Product Name: 2-(phenylethynyl)thiophene
• Synonyms: thiophene, 2-(2-phenylethynyl)-; Thiophene, 2-(phenylethynyl)-
• CAS NO: 4805-17-8
• Molecular Formula: C₁₂H₈S
• Molecular Weight: 184.2569
• Mol File: 4805-17-8.mol
• Article Data: 210

Chemical Properties

• Boiling Point: 308.5°C at 760 mmHg
• Flash Point: 103.4°C
• Density: 1.17g/cm³
• Vapor Pressure: 0.00124mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 2-(phenylethynyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(phenylethynyl)thiophene(4805-17-8)
• EPA Substance Registry System: 2-(phenylethynyl)thiophene(4805-17-8)

Safety Data

• Hazardous Substances Data: 4805-17-8(Hazardous Substances Data)

Usage

General Description

2-(phenylethynyl)thiophene is a chemical compound with the molecular formula C12H8S. It is a thiophene derivative with a phenylethynyl group attached to the 2-position of the thiophene ring. 2-(phenylethynyl)thiophene is often used as a building block in the synthesis of various organic materials such as conducting polymers, organic semiconductors, and optoelectronic devices. Its unique structure and properties make it a valuable tool in the field of material science and organic chemistry. The compound exhibits good electron transport properties and is often utilized in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells. Additionally, 2-(phenylethynyl)thiophene has been studied for its potential use in medical imaging due to its fluorescent properties and bioconjugation capabilities.

Upstream product

• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 6165-68-0 thiophene boronic acid 
• 96-43-5 2-thienyl chloride 
• 536-74-3 phenylacetylene 
• 3437-95-4 2-Iodothiophene 
• 637-44-5 phenylpropyolic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 201230-82-2 carbon monoxide 
• 98-03-3 thiophene-2-carbaldehyde 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 337512-22-8 3-(2-thienoyl)cinnoline 
• 133844-84-5 2-methyl-4-(thien-2-yl)but-3-yn-2-ol 
• 764-93-2 1-decyne 
• 932-88-7 1-iodo-2-phenylethyne 

Downstream Products

• 30135-07-0 1-phenyl-2-(2-thienyl)ethanedione 
• 18853-37-7 5,6-diphenyl-4H-cyclopenta--thiophen-4-one 
• 18853-36-6 2-phenyl 3-(2-thienyl)-<1H>-inden-1-one 
• 131269-20-0 2-(2'-thienyl)3-phenyl-<1H>-inden-1-one 
• 104314-03-6 3-phenyl-2-thiophen-2-yl-acrylic acid 
• 68969-38-0 1,1-diphenyl-2-(2-thienyl)-ethylene 
• 74827-17-1 (Z)-2-(1,2-diphenylethenyl)thiophene 
• 1421712-20-0 (E)-tributyl(1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-2-yl)vinyl)stannane 
• 1421712-21-1 (E)-tributyl(2-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(thiophen-2-yl)vinyl)stannane 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 

Relevant articles and documents

Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions

A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-

A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope

Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.