69818-23-1

Usage

InChI:InChI=1/C7H6O3/c1-10-5-2-3-6(8)7(9)4-5/h2-4H,1H3

Upstream product

• 3934-97-2 4-methoxycatechol 
• 150-76-5 4-methoxy-phenol 
• 104-94-9 4-methoxy-aniline 
• 150-19-6 O-methylresorcine 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 27688-86-4 3,4-dibenzyloxyphenol 
• 88755-15-1 1,2-dibenzyloxy-4-methoxybenzene 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 96-96-8 4-methoxy-2-nitroaniline 

Downstream Products

• 91061-89-1 2-Acetonyl-5-methoxy-o-benzochinol 
• 82822-28-4 2-(acetoxy)-5-methoxyphenyl acetate 
• 3934-97-2 4-methoxycatechol 
• 2876-18-8 2-methoxyphenazine 

Relevant academic research and scientific papers

Biomimetic Hydroxylation Catalysis Through Self-Assembly of a Bis(pyrazolyl)methane Copper-Peroxo Complex

We synthesised and characterised four copper complexes (with copper in the oxidation states I and II) with the bis(pyrazolyl) methane ligands HC(3-tBuPz)2(Py) and HC(3-tBuPz)2-(Qu). With the quinolinyl ligand (2-quinolinyl)bis(3-tert

Study on the degradation mechanism and pathway of benzene dye intermediate 4-methoxy-2-nitroaniline: Via multiple methods in Fenton oxidation process

Benzene dye intermediate (BDI) 4-methoxy-2-nitroaniline (4M2NA) wastewater has caused significant environmental concern due to its strong toxicity and potential carcinogenic effects. Reports concerning the degradation of 4M2NA by advanced oxidation process are limited. In this study, 4M2NA degradation by Fenton oxidation has been studied to obtain more insights into the reaction mechanism involved in the oxidation of 4M2NA. Results showed that when the 4M2NA (100 mg L-1) was completely decomposed, the TOC removal efficiency was only 30.70-31.54%, suggesting that some by-products highly recalcitrant to the Fenton oxidation were produced. UV-Vis spectra analysis based on Gauss peak fitting, HPLC analysis combined with two-dimensional correlation spectroscopy and GC-MS detection were carried out to clarify the degradation mechanism and pathway of 4M2NA. A total of nineteen reaction intermediates were identified and two possible degradation pathways were illustrated. Theoretical TOC calculated based on the concentration of oxalic acid, acetic acid, formic acid, and 4M2NA in the degradation process was nearly 94.41-97.11% of the measured TOC, indicating that the oxalic acid, acetic acid and formic acid were the main products. Finally, the predominant degradation pathway was proposed. These results could provide significant information to better understand the degradation mechanism of 4M2NA.

A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers

ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.

Associative chemosensing by fluorescent macrocycle-dye complexes-a versatile enzyme assay platform beyond indicator displacement

A label-free in situ method to monitor reactions in real time by using fluorescent supramolecular chemosensors based on cucurbit[8]uril is presented. It allows sensing of enzymatic activity, inhibitor and activator screening, and analyte detection with unprecedented versatility and high sensitivity.

Bioinspired organocatalytic aerobic C-H oxidation of amines with an ortho -quinone catalyst

A simple bioinspired ortho-quinone catalyst for the aerobic oxidative dehydrogenation of amines to imines is reported. Without any metal cocatalysts, the identified optimal ortho-quinone catalyst enables the oxidations of α-branched primary amines and cyclic secondary amines. Mechanistic studies have disclosed the origins of different performances of ortho-quinone vs para-quinone in biomimetic amine oxidations.

Catalytic oxygenation of various monophenols by copper(I) complexes with bis(pyrazolyl)methane ligands: Differences in reactivity

Three new mononuclear copper(I) complexes supported by the symmetric ligands 1,1′-methylenebis-1H-pyrazole (BPM), 1,1′-methylenebis(3-methyl-1H-pyrazole) (mBPM), and 1,1′-methylenebis(3,5-di-methyl-1H-pyrazole) (dmBPM) were synthesized as catalytic model systems of tyrosinase. The influence of various functional groups on the catalytic conversion of monophenols is investigated and the formation of the corresponding ortho-quinones is monitored using UV/vis and NMR spectroscopy. Comparison of various monophenols reveals the differences in reactivity which are analyzed and interpreted based on key intermediates of the mechanistic cycle.

Catalytic phenol hydroxylation with dioxygen: Extension of the tyrosinase mechanism beyond the protein matrix

A new catalyst (see structure) hydroxylates phenols with O2 via a stable side-on peroxide complex, which is similar to the active site of tyrosinase in terms of the ligand environment and its spectroscopic properties. The catalytic oxidation of phenols to quinones proceeds at room temperature in the presence of NEt3 and even non-native substrates can be oxidized catalytically. The reaction mechanism is analogous to that of the enzyme-catalyzed reaction. Copyright

Studies of the competing rates of catechol oxidation and suicide inactivation of tyrosinase

Tyrosinase oxidation of catechols to ortho-quinones is accompanied by suicide inactivation of the enzyme. The rates of these competing processes vary and depend on the nature of ring substituents. For a series of 4-substituted catechols the relationships between structure and reaction rates have been examined using multiple regression. Significant but different structure-rate relationships were found for each process. The oxidation rate (k1) is greatest for short hydrophobic substituents; there is an optimum substituent hydrophobicity (π 0.7) for the rate of inactivation (k2). ARKAT USA, Inc.

Synthesis and preliminary in vitro biological evaluation of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-mercaptophenol derivative designed as a novel bifunctional antimelanoma agent

We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl) sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activatable phenolic moiety and a GSH-re

Effects of electron-withdrawing substituents on DPPH radical scavenging reactions of protocatechuic acid and its analogues in alcoholic solvents

The DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity of protocatechuic acid (3,4-dihydroxybenzoic acid) and its related catechols was examined. Compounds possessing strong electron-withdrawing substituents showed high activity. NMR analysis of the reaction mixtures of catechols and DPPH radical in methanol showed the formation of methanol adducts. The results suggest that high radical scavenging activity of catechols in alcohol is due to a nucleophilic addition of an alcohol molecule on o-quinones, which leads to a regeneration of a catechol structure. Furthermore, the radical scavenging activity in alcohols would largely depend on the electron-withdrawing/donating substituents, since they affect the susceptibility toward nucleophilic attacks on o-quinone.