4783-86-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Phenoxypyridine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Phenoxypyridine is utilized as a precursor in the production of agrochemicals, aiding in the creation of compounds that can protect crops from pests and diseases.
Used in Dye Industry:
4-Phenoxypyridine is employed as a starting material in the preparation of dyes, where its chemical structure allows for the development of colorants with specific properties for various applications.
Used in Drug and Insecticide Synthesis:
As a precursor, 4-Phenoxypyridine is crucial in the synthesis of drugs and insecticides, providing a foundation for the creation of compounds that address specific medical and agricultural needs.

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

Upstream product

• 626-61-9 4-Chloropyridine 
• 139-02-6 sodium phenoxide 
• 100-67-4 potassium phenolate 
• 5421-92-1 1-(4-pyridyl)pyridinium chloride hydrochloride 
• 108-95-2 phenol 
• 75-05-8 acetonitrile 
• 163632-01-7 1-cyclopropyl-4-phenoxy-1,2,3,6-tetrahydropyridine 
• 15854-87-2 4-iodopyridine 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 626-64-2 pyridin-4-ol 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 504-24-5 4-aminopyridine 
• 108-96-3 4-pyridone 

Downstream Products

• 64890-22-8 4-(N-methyl-N-phenylamino)pyridine 
• 1122-58-3 dmap 
• 13556-71-3 N-benzyl-4-aminopyridine 
• 2767-90-0 4-piperidinylpyridine 
• 34844-87-6 4-(cyclohexylamino)pyridine 
• 35215-28-2 N-butylpyridin-4-amine 
• 101975-74-0 1-methyl-4-phenoxypyridinium iodide 
• 504-24-5 4-aminopyridine 
• 22961-45-1 N-phenylpyridin-4-amine 
• 75571-24-3 4-phenoxy-1,2,3,6-tetrahydro-pyridine 
• 4783-83-9 4-nitrophenyl-4-pyridyl ether 
• 80028-27-9 ethyl N-(4-pyridyl)nipecotate 
• 102877-78-1 4-(4-pyridinyloxy)aniline 
• 41661-47-6 piperidin-4-one 

Relevant academic research and scientific papers

Cu-based nanoalloys in the base-free ullmann heterocyle-aryl ether synthesis

We report the first liquid-liquid Ullmann etherification process mediated not only by oxidatively stable Cu but also by CuZn and CuSn nanoparticle catalysts in conjunction with microwave heating that also avoids the use of solid and expensive bases. Condi

Copper(0) in the Ullmann heterocycle-aryl ether synthesis of 4-phenoxypyridine using multimode microwave heating

The action of nanoparticulate copper catalysts with a mean particle size of 10 nm in the Ullmann ether synthesis is reported using multimode microwave heating and employing stable chloropyridine salts and unactivated phenol, with stabilized copper nanopar

Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer

Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.

N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions

Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.

Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Synthesis of copper nanoparticles supported on a microporous covalent triazine polymer: An efficient and reusable catalyst for O-arylation reaction

Copper nanoparticles were supported on a microporous covalent triazine polymer prepared by the Friedel-Crafts reaction (Cu@MCTP-1). The resulting material was characterized by powder X-ray diffraction, thermogravimetric analysis, N2 adsorption-desorption isotherms at 77 K, transmission electron microscopy, X-ray photoelectron spectroscopy, and inductively coupled plasma optical emission spectroscopy, and Cu particles with an average size of 3.0 nm and a BET total surface area of ca. 1002 m2 g-1 were obtained. Cu@MCTP-1 was evaluated as a heterogeneous catalyst for the Ullmann coupling of O-arylation over a series of aryl halides and phenols without employing expensive ligands or inert atmosphere, which produced an excellent yield of the corresponding diaryl ethers. The catalyst could be recovered by simple centrifugation and was reusable at least five times with only a slight decrease in catalytic activity.

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.

Graphene oxide grafted with Pd17Se15 nano-particles generated from a single source precursor as a recyclable and efficient catalyst for C-O coupling in O-arylation at room temperature

The Pd17Se15 nanoparticles, synthesized for the first time from a single source precursor [Pd(L)Cl2] {L = 1,3-bis(phenylselenyl)propan-2-ol} and grafted onto graphene oxide, show high catalytic activity in C-O coupling between aryl/heteroaryl chlorides/bromides and phenol at room temperature (Pd loading 1 mol%; yield up to 94%).

New Cu-based catalysts supported on TiO2 films for Ullmann SNAr-type C-O coupling reactions

New routes for the preparation of highly active TiO2-supported Cu and CuZn catalysts have been developed for C-O coupling reactions. Slurries of a titania precursor were dip-coated onto glass beads to obtain either structured mesoporous or non-porous titania thin films. The Cu and CuZn nanoparticles, synthesized using a reduction by solvent method, were deposited onto calcined films to obtain a Cu loading of 2 wt %. The catalysts were characterized by inductively coupled plasma (ICP) spectroscopy, temperature-programmed oxidation/reduction (TPO/TPR) techniques, 63Cu nuclear magnetic resonance (NMR) spectroscopy, X-ray diffraction (XRD), scanning and transmission electron microscopy (S/TEM-EDX) and X-ray photo-electron spectroscopy (XPS). The activity and stability of the catalysts obtained have been studied in the C-O Ullmann coupling of 4-chloropyridine and potassium phenolate. The titania-supported nanoparticles retained catalyst activity for up to 12 h. However, catalyst deactivation was observed for longer operation times due to oxidation of the Cu nanoparticles. The oxidation rate could be significantly reduced over the CuZn/TiO2 catalytic films due to the presence of Zn. The 4-phenoxypyridine yield was 64 % on the Cu/nonporous TiO2 at 120 °C. The highest product yield of 84 % was obtained on the Cu/mesoporous TiO2 at 140 °C, corresponding to an initial reaction rate of 104 mmol gcat-1 s-1. The activation energy on the Cu/mesoporous TiO2 catalyst was found to be (144±5) kJ mol-1, which is close to the value obtained for the reaction over unsupported CuZn nanoparticles (123±3 kJ mol-1) and almost twice the value observed over the catalysts deposited onto the non-porous TiO2 support (75±2 kJ mol-1). Copyright