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

• 91228-44-3 2-thienylphenyliodonium tosylate 
• 536-74-3 phenylacetylene 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 337512-22-8 3-(2-thienoyl)cinnoline 
• 33675-51-3 2-(bromoethynyl)thiophene 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 73163-70-9 2-Phenyl-1-thiophen-2-yl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 73163-73-2 1-Phenyl-2-thiophen-2-yl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 3437-95-4 2-Iodothiophene 
• 13146-23-1 copper(I) phenylacetylenide 
• 1003-09-4 2-bromothiophene 
• 201230-82-2 carbon monoxide 
• 1007-47-2 (phenylethynyl)dimethylaluminum 
• 527-72-0 2-thiophenylcarboxylic acid 

Downstream Products

• 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 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 28540-70-7 2-phenethylthiophene 
• 3783-65-1 (Z)-2-(β-styryl)thiophene 
• 68969-38-0 1,1-diphenyl-2-(2-thienyl)-ethylene 
• 74827-17-1 (Z)-2-(1,2-diphenylethenyl)thiophene 
• 65-85-0 benzoic acid 
• 6602-63-7 (pyridin-2-yl)(thiophen-2-yl)methanone 

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-

Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes

This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.