42545-43-7

Usage

Uses

Used in Organic Electronics:
2-(4-Methoxyphenyl)thiophene is used as a key component in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs), due to its favorable electronic properties.
Used in Materials Science:
In the field of materials science, 2-(4-Methoxyphenyl)thiophene is utilized as a building block for the synthesis of novel materials with tailored properties, such as high-performance polymers and advanced materials for energy storage and conversion.
Used in Pharmaceutical Industry:
2-(4-Methoxyphenyl)thiophene is used as a starting material or intermediate in the synthesis of various pharmaceuticals, leveraging its potential biological activities and chemical versatility.
Used in Dye Synthesis:
2-(4-Methoxyphenyl)thiophene is employed as a precursor in the production of dyes with specific color characteristics and properties, suitable for applications in colorants, pigments, and other dye-related industries.
Used in Medicinal Chemistry Research:
Due to its potential to exhibit interesting biological activities, 2-(4-Methoxyphenyl)thiophene is a subject of interest in medicinal chemistry research, where it can be further modified and optimized for the development of new therapeutic agents.

InChI:InChI=1/C11H10OS/c1-12-10-6-4-9(5-7-10)11-3-2-8-13-11/h2-8H,1H3

Upstream product

• 188290-36-0 thiophene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 81745-84-8 2-thienylzinc chloride 
• 96-43-5 2-thienyl chloride 
• 100-66-3 methoxybenzene 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 733-53-9 p-methoxyphenyl(phenyl)iodonium tetrafluoroborate 
• 53034-24-5 2-thienyllead(IV) triacetate 
• 2665-61-4 (p-methoxyphenyl)(phenyl)iodonium bromide 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 4456-36-4 di(p-methoxyphenyl)tellurium dichloride 
• 91228-44-3 2-thienylphenyliodonium tosylate 

Downstream Products

• 29886-65-5 4-thiophen-2-yl-phenol 
• 83495-25-4 5,5'-Bis-(4-methoxy-phenyl)-[2,3']bithiophenyl 
• 38401-67-1 2-formyl-5-(4-methoxyphenyl)thiophene 
• 166964-20-1 5-(4-Methoxyphenyl)-2-thiophenesulfonyl chloride 
• 1160457-06-6 C₁₈H₂₀O₃S 
• 1041011-51-1 butyl (E)-3-[5-(4-methoxyphenyl)-2-thienyl]-2-propenoate 
• 1257985-12-8 triisopropyl((5-(4-methoxyphenyl)thiophen-2-yl)ethynyl)silane 
• 1360187-08-1 2-(4-methoxyphenyl)-5-(4-trifluoromethylphenyl)thiophene 
• 1401352-28-0 2-butyl-5-(5-(4-methoxyphenyl)thiophen-2-yl)furan 
• 59086-11-2 2-(4-methoxyphenyl)-5-phenylthiophene 

Relevant academic research and scientific papers

Organozinc-mediated direct cross-coupling under microwave irradiation

We report a direct cross-coupling reaction between (het)aryl pivalates/tosylates and di(het)arylzinc species in 2-methyltetrahydrofuran/N-methyl pyrrolidone (1:1), which occurs via C–O bond cleavage under microwave irradiation. The reaction takes place smoothly in short reaction times without the addition of any catalyst or ligand. The reaction is suitable for a broad scope of substrates and exhibits good functional group compatibility, utilizes a simple work-up procedure, and gives the desired products in high purity.

Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction

Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]

Fabrication of Graphitic Carbon Nitride-Based Film: An Emerged Highly Efficient Catalyst for Direct C—H Arylation under Solar Light

Photoredox C—H bond formation can proceed in aerobic environment under solar light and has therefore become attractive. Nowadays, different types of expensive novel metal complexes and nanomaterials have been urbanized as photocatalysts for direct C—H bon

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents

Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].

Aerobic Cu and amine free Sonogashira and Stille couplings of aryl bromides/chlorides with a magnetically recoverable Fe3O4@SiO2 immobilized Pd(II)-thioether containing NHC

Two value added C–C cross coupling reactions; Sonogashira and Stille couplings were achieved at milder conditions in the catalytic presence of a magnetically recoverable heterogeneous catalyst Fe3O4@SiO2@NHC^SPh-Pd(II). The catalyst was earlier reported for Suzuki-Miyaura reaction, and as an extension of its catalytic efficiency, the Stille and Sonogashira cross coupling reactions under aerobic condition has been explored in present report. The Sonogashira coupling of aryl bromides and terminal alkynes produced an excellent yield (~96% at 0.25 mol% Pd) of the desired coupling product under copper and amines free conditions. Moreover, an excellent Stille coupling of readily available and more latent aryl chlorides and trialkylstannane was obtained (yields up to 95% at 0.25 mol% Pd) in absence of toxic fluorides additives. The broad substrate scope of the catalyst for both the coupling reactions and the magnetically recoverable feature of catalyst make this reaction highly desirable for industrial applications of present heterogeneous catalysis.

Immobilized Pd on a NHC functionalized metal–organic framework MIL-101(Cr): an efficient heterogeneous catalyst in Suzuki?Miyaura coupling reaction in water

A novel Pd?NHC functionalized metal–organic framework (MOF) based on MIL-101(Cr) was synthesized and used as an efficient heterogeneous catalyst in the C-C bond formation reactions. Using this heterogeneous Pd catalyst system, the Suzuki?Miyaura coupling reaction was accomplished well in water, and coupling products were obtained in good to excellent yields in short reaction time. The Pd?NHC?MIL-101(Cr) was characterized using some different techniques, including Fourier transform-infrared, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy (TEM), X-ray photoelectron spectroscopy, inductively coupled plasma and elemental analysis. The microscopic techniques showed the discrete octahedron structure of MIL-101(Cr), which is also stable after chemical modification process to prepare the catalyst system. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the structure of the catalyst, while no reducing agent was used. It seems that the NHC groups and imidazolium moieties in the structure of the MOF can reduce Pd (II) to Pd (0) species. This modified MOF substrate can also prevent aggregation of Pd nanoparticles, resulting in high stability of them in organic transformation. The Pd?NHC?MIL-101(Cr) catalyst system could be simply extracted from the reaction mixture, providing an efficient synthetic method for the synthesis of biaryls derivatives using the aforementioned coupling reaction. The Pd?NHC?MIL-101(Cr) catalyst could be recycled in this organic reaction with almost consistent catalytic efficiency.

One-step synthesis of magnetically recyclable palladium loaded magnesium ferrite nanoparticles: application in synthesis of anticancer drug PCI-32765

Novel Palladium nanoparticles supported nano Magnesium ferrite catalyst (Pd/MgFe2O4) was synthesized by one-step ultrasound assisted coprecipitation. In-situ formed by-products assisted salt cage calcination approach was employed to

Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross-Coupling Reactions

Silk fibroin supported Pd (Pd/SF) has been prepared and used as catalyst in Suzuki–Miyaura cross-coupling reactions in water/ethanol (4:1 v/v) mixture. The reactions proceed rapidly with aryl iodides and boronic acids with different electronic properties using low metal loading (0.38 mol-%). Pd/SF exhibits better recyclability compared to other biopolymer-supported Pd catalysts, up to nineteen cycles without loss of activity.