1657-55-2

Usage

Uses

Used in Plastics and Polymer Industry:
4,4'-Ethylenedianisole is used as a monomer for the production of poly(arylene ether) resins, which are high-performance thermoplastic materials. These resins are favored for their excellent mechanical, thermal, and chemical properties, making them suitable for a wide range of applications within the industry.
Used in Chemical Synthesis:
4,4'-Ethylenedianisole is utilized as a building block in the synthesis of various specialty chemicals and polymers. Its role in chemical synthesis allows for the creation of a diverse array of products that can be tailored for specific applications and industries.

Upstream product

• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 3613-53-4 1-((benzyloxy)methyl)-4-methoxybenzene 
• 920-39-8 isopropylmagnesium bromide 
• 64-17-5 ethanol 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 17004-42-1 1,2-bis(4-methoxybenzyl)disulfide 
• 4705-34-4 4,4'-dimethoxystilbene 
• 13057-17-5 bromethyl methyl ether 
• 2746-25-0 p-Methoxybenzyl bromide 
• 4852-26-0 3-pentylmagnesium bromide 
• 74-85-1 ethene 
• 100-66-3 methoxybenzene 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 

Downstream Products

• 6052-84-2 4,4'-ethylenediphenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 34036-55-0 1,2-bis(3-acetyl-4-methoxyphenyl)ethane 
• 785-78-4 4-phenethylacetophenone 
• 85-01-8 phenanthrene 
• 101133-41-9 bis(3-nitro-4-hydroxyphenyl)ethane 
• 22428-33-7 bis(3-amino-4-hydroxyphenyl)ethane 
• 105985-29-3 C₂₀H₂₂O₂ 
• 1426234-57-2 1,2-bis(4-(prop-1-en-1-yloxy)phenyl)ethane 
• 1426234-60-7 1-(2,2-diethyl-4-methylcyclobutoxy)-4-(4-(prop-1-en-1-yloxy)phenethyl)benzene 
• 1426234-61-8 1,2-bis(4-(2,2-diethyl-4-methylcyclobutoxy)phenyl)ethane 
• 159846-83-0 C₁₇H₁₈O₂ 

Relevant academic research and scientific papers

Solar light induced carbon-carbon bond formation via TiO2 photocatalysis

Solar light irradiation of a TiO2 suspension in MeCN containing maleic anhydride and 4-methoxybenzyl(trimethyl)silane gives benzylated succinic acid (or anhydride) on a gram scale.

Molybdenum-Catalyzed Deoxygenation Coupling of Lignin-Derived Alcohols for Functionalized Bibenzyl Chemicals

With the growing demand for sustainability and reducing CO2 footprint, lignocellulosic biomass has attracted much attention as a renewable, carbon-neutral and low-cost feedstock for the production of chemicals and fuels. To realize efficient utilization of biomass resource, it is essential to selectively alter the high degree of oxygen functionality of biomass-derivates. Herein, we introduced a novel procedure to transform renewable lignin-derived alcohols to various functionalized bibenzyl chemicals. This strategy relied on a short deoxygenation coupling pathway with economical molybdenum catalyst. A well-designed H-donor experiment was performed to investigate the mechanism of this Mo-catalyzed process. It was proven that benzyl carbon-radical was the most possible intermediate to form the bibenzyl products. It was also discovered that the para methoxy and phenolic hydroxyl groups could stabilize the corresponding radical intermediates and then facilitate to selectively obtain bibenzyl products. Our research provides a promising application to produce functionalized aromatics from biomass-derived materials.

Synthesis of ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid and their anticorrosive effect on carbon steel in 3%NaCl solution

The inhibition performance of the newly synthesized Ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid (ETPA) toward carbon steel in 3% NaCl was investigated at different concentrations using potentiodynamic polarization (PDP) and impedance spectroscopy (EIS) methods. It was found that the inhibition capability was increased with increasing inhibitor dose and reach 92% at 10?3 mol/L. Also, Polarization curves showed that ETPA acts as a mixed type inhibitor with predominantly control of anodic reaction. The new inhibitor was investigated by different spectroscopic methods such as 1H, 13C and 31PNMR. The quantum parameters such as absolute electronegativity (χ), energy gap ΔE (EHOMO-ELUMO), global softness (σ), global hardness (η), electrophilicity index (ω) and the number of transfer electrons (ΔN) are calculated by density functional theory (DFT). The experimental also correlated with density functional theory results. The calculations show that ETPA has high density of negative charge located on the oxygen atoms of the phosphonate group facilitating the adsorption of ETPA on the surface of carbon steel. The inhibition efficiency of ETPA was discussed in terms of blocking of electrode surface by adsorption of ETPA molecules through active centers. The adsorption of ETPA on the surface of carbon steel obeyed the Langmuir isotherm paradigm.

Boron carbonitride photocatalysts for direct decarboxylation: The construction of C(sp3)-N or C(sp3)-C(sp2) bonds with visible light

A metal-free protocol is established for the decarboxylative N-H or C(sp2)-H functionalization of acidsviametal-free boron carbon nitride (BCN) photocatalysis, delivering the desired products under ambient conditions. This methodology is applicable to the late-stage modification of pharmaceutical molecules and gram-scale experiments as well as in the recovery and reuse of the photocatalysts without the loss of reactivity. The developed photochemical reaction system fulfills the requirements of green and sustainable chemistry.

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.

Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols

Dibenzyls are essential building blocks that are widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we report an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and dimethyl oxalate assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary alcohols are tolerated.

Enantioselective Radical SN2-Type Alkylation of Morita-Baylis-Hillman Adducts Using Dual Photoredox/Palladium Catalysis

An enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita-Baylis-Hillman (MBH) adducts has been reported. The SN2-type products are predominant. This reaction is enabled by dual photoredox/palladium catalysis. The alkylation products are provided in good yields with good regio- and enantioselectivity. The use of Ding's spiroketal-based bis(phosphine) (SKP) ligand is crucial to achieving satisfactory regio- and enantioselectivity. The resultant α,β-unsaturated ester can be easily reduced to a synthetically useful chiral allyl alcohol.

A heavy-metal-free desulfonylative Giese-type reaction of benzothiazole sulfones under visible-light conditions

A visible-light-induced desulfonylative Giese-type reaction has been developed. Essential to the success is the employment of Hantzsch ester to activate benzothiazole sulfones without any heavy-metal additives. Not only benzylic benzothiazole sulfones but also alkyl ones were viable substrates and reacted with electron-deficient alkenes and a propiol amide.

Photocatalytic Reductive C-O Bond Cleavage of Alkyl Aryl Ethers by Using Carbazole Catalysts with Cesium Carbonate

Methods to activate the relatively stable ether C-O bonds and convert them to other functional groups are desirable. One-electron reduction of ethers is a potentially promising route to cleave the C-O bond. However, owing to the highly negative redox potential of alkyl aryl ethers (Ered -2.6 V vs SCE), this mode of ether C-O bond activation is challenging. Herein, we report the visible-light-induced photocatalytic cleavage of the alkyl aryl ether C-O bond using a carbazole-based organic photocatalyst (PC). Both benzylic and non-benzylic aryl ethers underwent C-O bond cleavage to form the corresponding phenol products. Addition of Cs2CO3 was beneficial, especially in reactions using a N-H carbazole PC. The reaction was proposed to occur via single-electron transfer (SET) from the excited-state carbazole to the substrate ether. Interaction of the N-H carbazole PC with Cs2CO3 via hydrogen bonding exists, which enables a deprotonation-assisted electron-transfer mechanism to operate. In addition, the Lewis acidic Cs cation interacts with the substrate alkyl aryl ether to activate it as an electron acceptor. The high reducing ability of the carbazole combined with the beneficial effects of Cs2CO3 made this otherwise formidable SET event possible.

Dehydrogenative Coupling of Benzylic and Aldehydic C-H Bonds

A photoinduced dehydrogenative coupling reaction between benzylic and aldehydic C-H bonds is reported. When a solution of an alkylbenzene and an aldehyde in ethyl acetate is irradiated with visible light in the presence of iridium and nickel catalysts, a coupled α-aryl ketone is formed with evolution of dihydrogen. An analogous C-C bond forming reaction occurs between a C-H bond next to the nitrogen of an N-methylamide and an aldehydic C-H bond to produce an α-amino ketone. These reactions provide a straightforward pathway from readily available materials leading to valued structural motifs of pharmacological relevance.