59007-04-4

Usage

Uses

Used in Fuel Cell Applications:
4'-methoxy[1,1'-biphenyl]-2,5-diol is used as a synthetic precursor for the preparation of side-chain-type sulfonated poly(arylene ether ketone) with pendant sulfoalkyl groups. This polymer is specifically designed for use as an electrolyte in direct methanol fuel cells, where it plays a crucial role in facilitating the efficient and selective transport of methanol and protons, thereby enhancing the overall performance and efficiency of the fuel cell.
In the Chemical Industry:
4'-methoxy[1,1'-biphenyl]-2,5-diol is utilized as an intermediate in the synthesis of various specialty chemicals, including pharmaceuticals, dyes, and other organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable component in the development of new molecules with specific properties and applications.
In the Polymer Industry:
4'-methoxy[1,1'-biphenyl]-2,5-diol is also used as a monomer in the polymer industry, where it can be polymerized to form polymers with specific properties, such as enhanced thermal stability, mechanical strength, or chemical resistance. These polymers can be used in a wide range of applications, from automotive components to electronic devices.
In the Pharmaceutical Industry:
4'-methoxy[1,1'-biphenyl]-2,5-diol may be employed as a building block in the development of new pharmaceutical compounds, particularly those with antioxidant or anti-inflammatory properties. Its ability to form stable complexes with other molecules makes it a promising candidate for the design of drugs targeting specific biological pathways.
In the Cosmetics Industry:
Due to its antioxidant properties, 4'-methoxy[1,1'-biphenyl]-2,5-diol can be used in the cosmetics industry as an additive to help protect skin from oxidative stress and environmental damage. It may also be used in the formulation of skincare products that aim to improve skin health and appearance.

Upstream product

• 479075-37-1 2-(4-methoxy-phenyl)-cyclohexane-1,4-dione 
• 446312-09-0 2-bromomethyl-2-(4-methoxy-phenyl)-cyclopentane-1,3-dione 
• 106-51-4 p-benzoquinone 
• 104-94-9 4-methoxy-aniline 
• 123-31-9 hydroquinone 
• 80336-70-5 2-bromo-1,1-dimethoxy-1-(4-methoxyphenyl)ethane 
• 30100-35-7 p-anisyl-p-benzoquinone 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 446312-07-8 2-[2-bromo-1-methoxy-1-(4-methoxy-phenyl)-ethyl]-2-trimethylsilanyloxy-cyclobutanone 

Downstream Products

• 1185-39-3 2,2-dimethyl-n-valeric acid 

Relevant academic research and scientific papers

Hydroquinone-Based Biarylic Polyphenols as Redox Organocatalysts for Dioxygen Reduction: Dramatic Effect of Orcinol Substituent on the Catalytic Activity

A series of 18 new biaryls has been synthesized and investigated with regard to their organocatalytic efficiency. They consist of a hydroquinone core linked to a phenol or a resorcinol moiety. It is shown that the resorcinol moiety substituted on its meta position has a strong impact on the catalytic activities of these compounds towards the reduction of dioxygen by diethylhydroxylamine (DEHA) in aqueous medium. While the derivative consisting of the two cores spaced by three methylene units is completely inactive, substitution on the hydroquinone part leads to tremendously active catalysts, especially the biaryl consisting of methoxyhydroquinone-orcinol. Two mechanisms are proposed to explain the dramatic efficiency of the novel hydroquinone-based biarylic polyphenols for the catalytic reduction of dioxygen, both considering the influence of the orcinol moiety on the semiquinone anion intermediate. As a first hypothesis, this substituent could promote its direct reduction by DEHA to regenerate the hydroquinone, which will react again to regenerate the semiquinone. On the other hand, an intramolecular hydrogen bond could enhance the reactivity of the semiquinone anion toward dioxygen by an addition–elimination mechanism. In this case, the elimination would provide the corresponding quinone but, since the reduction of the quinones by DEHA is much slower than the observed kinetics, a reduction by DEHA prior to the elimination has to be considered to generate the semiquinone anion instead of the quinone. (Figure presented.).

Visible-Light-Induced, Catalyst-Free Radical Arylations of Arenes and Heteroarenes with Aryldiazonium Salts

In the absence of a photocatalyst and other additives, the radical arylation of diverse arenes and heteroarenes has been achieved with aryldiazonium salts under visible-light irradiation from a blue light-emitting diode (LED). Although the course of some reactions can be rationalized by the formation of strongly light-absorbing charge-transfer (CT) complexes between the diazonium ion and the aromatic substrate, several further examples indicated that the simple presence of an aromatic substrate, showing only weak interactions to the diazonium ion, is fully sufficient to enable product formation.

Direct UV-written highly fluorinated aromatic-aliphatic copolyethers for optical waveguides

A bisphenol monomer (4-methoxy) phenylhydroquinone (Me-HQ) was prepared and further polymerized with 2,2,3,3,4,4,5,5,6,6,7,7-dodeca-fluoro-1,8-octanediol (12F-diol) and decafluorobiphenyl (DFBP) to obtain highly fluorinated aromatic-aliphatic copolyethers containing methoxy groups. After demethylation and the reaction with epoxy chloropropane, a series of novel highly fluorinated aromaticaliphatic copolyethers bearing epoxy groups (FA-APE EP) at different feed ratios of (Me-HQ)/(12F-diol) were obtained. The chemical structures of all the copolymers were analyzed by 1H NMR, 13C NMR and 19F NMR spectra. A series of highly fluorinated photoresists were prepared by composing of fluorinated copolyethers, diphenyliodonium salt as a photoacid generator (PAG) and solvent. After UV-curing, the cross-linked films exhibited excellent chemical resistance and high thermal stability (Td ranged from 230 to 278 -C). The refractive indices of the films could be controlled between 1.5127 and 1.4749 at 1550 nm by varying the feed ratio of comonomers. A clear negative pattern was obtained through direct UV exposure and chemical development. For waveguides without upper cladding, the propagation loss of the channel waveguides was measured to be 0.18 dB/cm at 1550 nm.

Novel access to cyclohexane-1,4-diones and 1,4-hydroquinones via radical 1,2-acyl rearrangement on 2-(halomethyl)cyclopentane-1,3-diones using cobaloxime-mediated electroreduction or tributyltin hydride

A new preparative access to synthetically useful cyclohexane-1,4-diones 2 and their oxidized analogues, hydroquinones 3, with the option of introducing alkyl and aryl substituents, was developed by radical 1,2-acyl rearrangement on 2-(halomethyl)cyclopentane-1,3-diones 1, accessible from 1,2-bis(trimethylsiloxy)cyclobutene and α-bromo ketone dimethyl acetals. The electroreduction of monoacetals of 1 in the presence of cobaloxime as a catalyst afforded the cyclohexane-1,4-dione monoacetals in good yields. The Bu3SnH-reduction of 2-aryl 1 under refluxing in benzene effected the rearrangement, affording 2, and when the reaction was prolonged, aromatization to 3 proceeded in moderate yields.

1,3-Dipolar Cycloaddition Reactions of 1,4-Benzoquinones with Nitrilimines

The cycloaddition reactions of some aryl conjugated p-benzoquinones with nitrilimines were studied.Depending upon the reaction conditions mono- and/or bis- adducts were isolated only from carbon-carbon double bond.The structure determination was unequivocally established by an X-ray analysis carried out on a bis-adduct.The observed regio-, as well as site-selectivity was qualitatively correlated with frontier molecular orbitals of the reacting species.

Mechanism of the Oxidation of NADH by Quinones. Energetics of One-Electron and Hydride Routes

The kinetics of NADH oxidation by 7 o-benzoquinones and 14 p-benzoquinones were studied by using buffered aqueous solutions and UV/vis spectroscopy.For each quinone the rate law was first order in NADH and first order in quinone.The rate constants varied from 0.0745 to 9220 M-1s-1.Variation of the pH from 6 to 8 gave no change in rate.The use of 4-D and 4,4-D2NADH revealed kinetic isotope effects.The dideutero data gave kH/kD in the range 1.6-3.1 for p-quinones and 4.2 for 3,5-di-tert-butyl-o-quinone.When p-quinones were used, the log k was a linear function of Eo for the quinone/hydroquinone monoanion (Q/QH(1-)) couple with a slope of 16.9 V-1. o-Quinones reacted about 100 times more rapidly, but the same linear relationship with a slope of 16.4 V-1 was observed.Comparisons to data for one-electron-transfer reactions indicate that such mechanisms are not involved.A hydride-transfer mechanism accommodates all the data, and rate-limiting hydrogen atom transfer followed by electron transfer cannot be ruled out.

Stabilized polyglycol for high temperatures

A composition comprising a poly-alkyleneglycol is stablized against molecular degradation and viscosity loss at elevated temperatures by about 0.1 to about 10% by weight of an arylhydroquinone such as p-acetylphenylhydroquinone.