2176-45-6

Usage

Uses

Used in Organic Synthesis:
3-Phenoxypyridine is utilized as a key intermediate in organic synthesis for the production of a variety of chemical compounds. Its unique structure allows for the creation of diverse molecules with potential applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Phenoxypyridine serves as an intermediate, contributing to the development of new drugs. Its potential biological activities make it a promising candidate for further research and development in medicinal chemistry.
Used as a Ligand in Metal-Catalyzed Reactions:
3-Phenoxypyridine is employed as a ligand in metal-catalyzed reactions, enhancing the efficiency and selectivity of these processes. Its role in catalysis is crucial for the synthesis of complex organic molecules and the advancement of catalytic methodologies.
Used as an Effective Solvent in Chemical Processes:
Recognized for its solvent properties, 3-Phenoxypyridine is applied across various chemical processes. Its ability to dissolve a wide range of substances makes it an indispensable component in the laboratory and industrial settings, facilitating numerous chemical reactions and processes.

InChI:InChI=1/C11H9NO/c1-2-5-10(6-3-1)13-11-7-4-8-12-9-11/h1-9H

Upstream product

• 109-00-2 3-HYDROXYPYRIDINE 
• 1120-90-7 3-iodopyridine 
• 100-67-4 potassium phenolate 
• 372-47-4 3-Fluoropyridine 
• 626-60-8 3-Chloropyridine 
• 108-86-1 bromobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 591-50-4 iodobenzene 
• 108-95-2 phenol 
• 108-90-7 chlorobenzene 
• 1692-25-7 3-pyridylboronic acid 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 626-55-1 3-Bromopyridine 

Downstream Products

• 75580-04-0 2-methyl-5-phenoxypyridine 
• 76167-46-9 2-methyl-3-phenoxypyridine 
• 18085-61-5 3-(4-bromophenoxy)pyridine 
• 109811-63-4 1-phenethyl-5-phenoxy-1H-pyridin-2-one 
• 54629-96-8 4-methyl-3-phenoxypyridine 
• 114078-07-8 (E)-methyl-2-(3'-phenoxypyrid-4'-yl)-3-methoxyacrylate 
• 32967-12-7 3-phenoxypyridine 1-oxide 
• 694471-97-1 4-(pyridin-3-yloxy)-benzenesulfonyl chloride 
• 28232-53-3 3-(4-nitro-phenoxy)-pyridine 
• 40604-27-1 3-(2,4-dinitro-phenoxy)-pyridine 
• 110532-45-1 1-phenethyl-3-phenoxy-pyridinium; bromide 

Relevant academic research and scientific papers

The First C?Cl Activation in Ullmann C?O Coupling by MOFs

It was found that introduction of only 0.03 mol % Ag(I) into the framework of Cu3(BTC)2 ? xH2O in maghemite anchored CuBTC activated the inert CuBTC astonishingly to exhibit unexpected high catalytic activity for C?Cl activation in coupling of chloroarenes with phenols without the use of expensive ligands. This is the first application of mixed-metal MOFs in the C?X activation. Putting reusability and activity together, a TON over 15000 was obtained which is the highest TON compared with all its precedents even better than the results by Pd catalysts.

A green approach for arylation of phenols using iron catalysis in water under aerobic conditions

The first efficient iron-catalyzed coupling of aryl iodides with phenols was developed exclusively with water as solvent. The reaction is performed with low cost and readily available FeCl3·6H2O and DMEDA catalytic system providing diaryl ethers in good to excellent yields. The effectiveness of this reaction was further revealed by compatibility with a wide range of functional groups. Moreover, the procedure is rendered simple as this transformation is carried out in the presence of air. Thus, the protocol represents a facile, economical and eco-friendly procedure to access diaryl ethers.

Ullmann Reaction Catalyzed by Heterogeneous Mesoporous Copper/Manganese Oxide: A Kinetic and Mechanistic Analysis

A heterogeneous copper oxide supported on mesoporous manganese oxide (meso Cu/MnOx) was explored for Ullmann-type cross-coupling reactions. An inverse micelle-templated evaporation-induced self-assembly method with in situ addition of copper was adopted to synthesize the mesoporous catalyst. Broad substrate scope and excellent functional group tolerability in C-O, C-N, and C-S bond formation reactions were observed using the optimized reaction conditions. The catalytic protocol was ligand free, and the catalyst was reusable without any significant loss of activity. The kinetic and Hammett analyses provided evidence for oxidative addition to a Cu(I) reaction center followed by nucleophilic addition and reductive elimination at the active copper oxide surface. Rate acceleration was observed for aryl halides with electron-withdrawing groups. The Hammett analysis determined ρ = +1.0, indicative of an oxidative addition, whereas the electronic effect in the phenol ring (ρ = -2.9) was indicative of coordination to a metal ion. Theoretically, the oxidative addition of the aryl halides is assisted by the ligand environment of the copper center. Relevant mechanistic implications are discussed on the basis of the experimental and computational results.

Visible-light-mediated synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts

With visible-light irradiation, a simple and metal-free photocatalytic system for the synthesis of diaryl ethers from arylboronic acids and diaryliodonium salts has been developed. The reaction proceeded in high yield for a range of different substrates in the presence of eosin Y under mild reaction conditions.

Synthesis of benzofuro[3,2-b]pyridines via palladium-catalyzed dual C-H activation of 3-phenoxypyridine 1-oxides

An efficient oxidative cyclization to straightforward synthesis of benzofuro[3,2-b]pyridine 1-oxides with high regioselectivity via Pd-catalyzed intramolecular dual C-H activation was developed. The resulting products could be deoxygenated easily to the corresponding benzofuro[3,2-b]pyridines in excellent yields.

A counteranion triggered arylation strategy using diaryliodonium fluorides

A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic O-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstrating the compatibility of the arylation tactic with latent carbon nucleophiles.

Chemoselective and ligand-free synthesis of diaryl ethers in aqueous medium using recyclable alumina-supported nickel nanoparticles

An economical and eco-compatible ligand-free protocol for the synthesis of diaryl ethers has been developed using easily accessible alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst in aqueous medium along with a surfactant (SDS) and a mild base (K2CO3). Various sensitive functional groups like allyl, alkoxycarbonyl, formyl, oxo, chloro, bromo, amine and nitro were tolerated in the aforesaid method. Excellent chemoselectivity was demonstrated through competition experiments.

One-pot synthesis and applications of N-heteroaryl iodonium salts

An efficient one-pot synthesis of N-heteroaryl iodonium triflates from the corresponding N-heteroaryl iodide and arene has been developed. The reaction conditions resemble our previous one-pot syntheses, with suitable modifications to allow N-heteroaryl groups. The reaction time is only 30 min, and no anion exchange is required. The obtained iodonium salts were isolated in a protonated form, these salts can either be employed directly in applications or be deprotonated prior to use. The aryl groups were chosen to induce chemoselective transfer of the heteroaryl moiety to various nucleophiles. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields. N-Heteroarylation: An efficient one-pot synthesis of N-heteroaryl iodonium triflates from the corresponding N-heteroaryl iodide has been developed. The reactivity and chemoselectivity of these iodonium salts were demonstrated by selectively introducing a pyridyl moiety onto both oxygen and carbon nucleophiles in good yields.

An Ullmann C-O coupling reaction catalyzed by magnetic copper ferrite nanoparticles

Herein, an efficient method for the Ullmann C-O coupling reaction between various kinds of phenols and aryl halides, including amino, ketone, cyano, methyl, methoxy, fluoro, chloro and bromo derivatives, is described. The catalyst used, copper ferrite (CuFe2O4) nanoparticles, are easily made, air-stable, and of low cost. The catalyst can be recycled easily just by using an external magnet. Even in the presence of sensitive substituents, the reaction proceeds successfully to provide the desired products in high yields without protection of other functional groups. Copyright

Preparation of carbon nanotube-supported α-Fe2O 3@CuO nanocomposite: A highly efficient and magnetically separable catalyst in cross-coupling of aryl halides with phenols

Herein, we introduce the first magnetic CuO nanoparticles based on carbon nanotubes as a highly intriguing magnetic catalyst in Ullmann-type coupling of aryl halides with phenols. Two facile procedures were used for the preparation of this magnetically separable catalytic system. Having been treated with FeSO4 and then H2O2, nanotubes accommodated the resulting iron hydroxides on the walls. The resulting nanocomposite was then exposed to argon atmosphere at 450°C giving rise to a carbon nanotube-supported α-Fe2O3 compound. Ultimately, copper acetate was hydrolysed in the presence of CNT supported α-Fe 2O3 at 100°C and our novel catalyst was gained. Some spectroscopic and microscopic techniques such as Infrared spectroscopy (IR), X-ray diffraction spectroscopy (XRD), Vibrational sample magnetometry (VSM), Brunauer-Emmett-Teller (BET), Barrett-Joyner-Halenda (BJH), Inductively coupled plasma (ICP), Scanning electron microscopy (SEM) and Transmission electron microscopy (TEM) corroborated the structure of the catalyst. The catalyst synthesized showed good activity in C-O cross coupling reactions affording the highest rate of completion. Magnetic feature of the catalyst helped facile separation of it from the reaction medium. The catalyst could also be reused up to six times without any loss of its activity.