3402-85-5

Usage

Compound type

Aromatic compound.

Structure

Composed of a benzene ring with a methoxy group (–OCH3) and a p-tolyl group (–C6H4CH3) attached at the 1 and 4 positions, respectively.

Usage

Commonly used as a fragrance ingredient in perfumes, soaps, and other personal care products.

Potential applications

Synthesis of pharmaceuticals and organic compounds.

Health hazards

May pose health hazards if inhaled or ingested in large quantities.

Handling precautions

Should be handled with proper care and precautions.

InChI:InChI=1/C14H14O2/c1-11-3-5-13(6-4-11)16-14-9-7-12(15-2)8-10-14/h3-10H,1-2H3

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 106-44-5 p-cresol 
• 106-38-7 para-bromotoluene 
• 1122-93-6 potassium p-methoxyphenolate 
• 696-62-8 para-iodoanisole 
• 1122-95-8 sodium 4-methoxyphenolate 
• 62790-85-6 tert-Butyl(dimethyl)-(4-methylphenoxy)silane 
• 624-31-7 4-tolyl iodide 
• 150-76-5 4-methoxy-phenol 
• 7758-89-6 copper(I) chloride 
• 106-43-4 para-chlorotoluene 
• 623-12-1 4-chloromethoxybenzene 
• 5142-75-6 tri(p-tolyl)bismuth 
• 38342-84-6 methyl 4-(4-methoxyphenoxy)benzoate 

Downstream Products

• 150-76-5 4-methoxy-phenol 
• 875816-98-1 1-(2-methoxy-5-p-tolyloxy-phenyl)-ethanone 
• 106-44-5 p-cresol 
• 15791-03-4 1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 35094-91-8 4-(p-tolyloxy)phenol 
• 78725-47-0 4-(4-methoxyphenoxy)benzaldehyde 
• 3525-22-2 4'-(4-methoxyphenoxy)benzoic acid 

Relevant academic research and scientific papers

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.

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

Pd-Catalyzed Etherification of Nitroarenes

The Pd-catalyzed etherification of nitroarenes with arenols has been achieved using a new rationally designed ligand. Mechanistic insights were used to design the ligand so that both the oxidative addition and reductive elimination steps of a plausible catalytic cycle were facilitated. The catalytic system established here provides direct access to a range of unsymmetrical diaryl ethers from nitroarenes.

Aromatic ether compound or the sulfhydryl compound

[Problem] Aromatic ether compounds and aromatic sulfide compound of this new technology to[Solution] In general formula (1a), (1b), (1c) palladium or nickel compound or a phosphine compound represented by the compound comprising a transition metal compound in the presence of a transition metal catalyst, (A1) is represented by compounds having hydroxy carbon C a-OH or (A2) with a compound represented by the sulfhydryl carbon C a-SH, nitro group (- NO2 ) To react with an aromatic nitro compound (B), (A1) to the compound of the aromatic nitro compound (C1) or the reaction product of an aromatic ether compounds (B) hetero coupling (A2) of the compounds of the reaction product of an aromatic sulfide compound of an aromatic nitro compound (C2) generating (B) hetero coupling characterized by comprising the step of, aromatic ether compounds or aromatic sulfide compound. [Drawing] no

CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions

Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].

Exhaustive Reduction of Esters Enabled by Nickel Catalysis

We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of -CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C-O bonds are demonstrated.

A novel magnetic polyacrylonotrile-based palladium Core?Shell complex: A highly efficientcatalyst for Synthesis of Diaryl ethers

The present article describes the synthesis of a new magnetic polyacrylonitrile-based Pd catalyst involving polyacrylonitrile modified via 2-aminopyridine as an efficient support to immobilize Pd nanoparticles. The simple reusability, easy separation and high stability of this Pd complex make it an excellent candidate to generate a C–O bond via Ph-X activation which is a really important subject in achieving biologically active compounds. It is worth to note access to good and high yields as well as broad substrate scope have resulted from superior reactivity of this catalyst complex. Furthermore, the structure of the magnetic polyacrylonitrile-based heterogeneous catalyst was characterized by fourier transmission infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD). Also, its thermal properties were studied by thermogravimetric analysis (TGA).

Preparation method of diaryl ether compound

The invention relates to a preparation method of a diaryl ether compound. Particularly, under catalysis of chitosan supported cuprous oxide, an arylation reaction used for phenols is achieved, the corresponding diaryl ether compound is obtained, the technological condition is simple, the yield is good, operability is high, and wide functional group durability is achieved.

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

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.