1655-69-2

Usage

Uses

Used in Pesticide Production:
1-METHOXY-4-PHENOXY-BENZENE is utilized as a key component in the formulation of pesticides. Its chemical properties contribute to the effectiveness of these agricultural chemicals, enhancing crop protection and yield.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-METHOXY-4-PHENOXY-BENZENE serves as an essential intermediate in the synthesis of various drugs. Its unique structure allows for the creation of medicinal compounds with specific therapeutic properties.
Used as a Precursor in Chemical Manufacturing:
1-METHOXY-4-PHENOXY-BENZENE is recognized for its potential as a precursor in the manufacture of other chemicals. Its reactivity and compatibility with a range of chemical processes make it a valuable starting material for developing new chemical entities and products.

InChI:InChI=1/C13H12O2/c1-14-11-7-9-13(10-8-11)15-12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 139-02-6 sodium phenoxide 
• 108-86-1 bromobenzene 
• 150-76-5 4-methoxy-phenol 
• 108-95-2 phenol 
• 1122-95-8 sodium 4-methoxyphenolate 
• 100-66-3 methoxybenzene 
• 105904-57-2 2-Brom-4-methoxy-diphenylaether 
• 696-62-8 para-iodoanisole 
• 591-50-4 iodobenzene 
• 87545-50-4 2-(4-phenoxyphenoxy)ethanethiol 
• 74-88-4 methyl iodide 
• 1122-93-6 potassium p-methoxyphenolate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 150-76-5 4-methoxy-phenol 
• 42592-67-6 4,4'-bis-(4-methoxy-phenoxy)-benzophenone 
• 78725-47-0 4-(4-methoxyphenoxy)benzaldehyde 
• 831-82-3 4-Phenoxyphenol 
• 26002-36-8 1-iodo-4-(4-methoxyphenoxy)benzene 
• 791108-77-5 1-methoxy-2-nitro-4-phenoxy-benzene 
• 93434-70-9 1-(4-(4-methoxyphenoxy)phenyl)propan-1-one 
• 54916-28-8 1-[4-(4-methoxyphenoxy)phenyl]ethanone 
• 88112-86-1 3-<4-(4-methoxyphenoxy)benzoyl>acrylic acid 
• 94402-60-5 4-(4-methoxyphenoxy)phenacyl chloride 
• 15791-03-4 1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 108-95-2 phenol 
• 92-69-3 4-Phenylphenol 
• 13522-82-2 5-methoxy-[1,1'-biphenyl]-2-ol 

Relevant academic research and scientific papers

New access to cross-coupling reaction between arylsilanes or heteroarylsilanes and aryl halides mediated by a copper(I) salt

Copper(I) salt can be used as a promoter for the cross-coupling reactions between aryl- or heteroarylsilanes and aryl halides without a fluoride ion. Under these mild conditions, even a substrate containing a fluoride ion-sensitive silyloxyl group was employed directly.

Ullmann-type coupling reaction using metal-organic framework MOF-199 as an efficient recyclable solid catalyst

A highly porous metal-organic framework (MOF-199) was synthesized, and characterized by several methods including XRD, SEM, TEM, TGA, FT-IR, AAS, and nitrogen physisorption measurements. The MOF-199 was used as an efficient recyclable solid catalyst for the Ullmann-type reaction between aryl iodides and phenols to form diaryl ethers. High conversions were achieved for the transformation at the catalyst concentration of 5 mol%, in the presence of MeONa as a base. Due to the rare availability and the high cost, Cs 2CO3 should only be used for the case of deactivated aryl iodides or deactivated phenols. The MOF-199 catalyst could be facilely separated from the reaction mixture by simple filtration, and could be reused several times without a significant degradation in catalytic activity. The Ullmann-type reaction could only proceed in the presence of the solid MOF-199 catalyst, and the contribution from leached active species in the liquid phase, if any, was negligible.

Functionalization of graphene oxide with a hybrid P, N ligand for immobilizing and stabilizing economical and non-toxic nanosized CuO: an efficient, robust and reusable catalyst for the C-O coupling reaction in O-arylation of phenol

Herein, we report a promising graphene oxide (GO) anchored robust and thermally stable heterogeneous catalytic system containing the low cost and less toxic copper oxide as a catalytically active material for C-O coupling reactions. A hybrid ligand (i.e. PPh2-CH2-CH2-NH2) has been used for the first time for functionalization of the GO surface. This ligand grafted over GO sheets via covalent linkages acts as an efficient stabilizing and chelating agent for CuO nanoparticles through P and N donor sites to form the catalytic system (GO-PN-CuO). The powder X-ray diffraction (PXRD), infrared (IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TGA), Brunauer-Emmett-Teller (BET) studies, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM) and Raman spectroscopy confirmed the step-wise formation of GO-PN-CuO. The catalytic potential of GO-PN-CuO has been explored for the C-O coupling reactions of phenols with several aryl bromides and chlorides under mild reaction conditions. The covalent linkage of the hybrid ligand with GO sheets and the strong binding abilities of P, N donor sites with CuO render high stability to GO-PN-CuO. As a result, the catalytic system offers the advantage of recyclability up to five reaction cycles without any considerable loss in activity.

Synthesis and characterization of nano-cellulose immobilized phenanthroline-copper (I) complex as a recyclable and efficient catalyst for preparation of diaryl ethers, N-aryl amides and N-aryl heterocycles

Functionalized nanocellulose was prepared and employed for immobilization of phenanthroline-copper(I) complex to afford cellulose nanofibril grafted heterogeneous copper catalyst [CNF-phen-Cu(I)]. This nanocatalyst was well characterized using FT-IR, NMR, XRD, CHNS, AAS, TGA, EDX and SEM. The activities of the synthesized catalyst were examined in the synthesis of diaryl ethers via C-O cross-coupling of phenols and aryl iodides, as well as, the preparation of N-aryl amides and N-aryl heterocycles through C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. In this trend, various substrates containing electron-donating and electron-withdrawing groups were exploited to evaluate the generality of this catalytic protocol. Accordingly, the catalyst demonstrated remarkable catalytic efficiency for both C-N and C-O cross-coupling reactions, thereby resulting in good to excellent yields of the desired products. Furthermore, the recoverability experiments of the catalyst showed that it can be readily retrieved by simple filtration and successfully reused several times with negligible loss of its catalytic activity.

Light-Assisted Ullmann Coupling of Phenols and Aryl Halides: The Synergetic Effect Between Plasmonic Copper Nanoparticles and Carbon Nanotubes from Various Sources

Utilizing light and plastic wastes as resources to turn the wasted phenols and hazardous aryl halides into value added chemicals seems to be an attractive idea for alleviating the energy crisis and environmental problems. In this work, plasmonic copper nanoparticles (Cu NPs) were loaded onto carbon nanotubes (CNTs) from various sources including commercial CNTs and those derived from plastic wastes. Under visible-light irradiation, the catalyst could efficiently convert phenols and aryl halides to diaryl ethers. Similar with commercial CNTs, excellent activity is also achieved when utilizing CNTs derived from different kinds of plastic wastes as support for the system. Further investigation shows that the visible-light irradiation and light-excited plasmonic Cu NPs are necessary to inhibit the phenol degradation on CNTs and in turn promote the cross-coupling of phenol and aryl halides. Compared with metal oxides and other carbon materials, the excellent capability of CNTs to absorb light, to convert light to heat, and to adsorb both two reactants simultaneously are critical to enhance the activity of Cu NPs, achieving high yields of diaryl ethers. This study could provide a novel strategy for catalyst design and generate a more economically sustainable process.

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions

A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols

A new solvent-free procedure for C–O cross-coupling between phenols and aryl bromides comprising of Pd2(dba)3/ButBrettPhos catalytic system is efficient for substrates bearing donor or acceptor, as well as bulky substituents.

Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions

We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.