137-18-8

Usage

Uses

Used in Pharmaceutical Industry:
P-XYLOQUINONE is used as a key intermediate in the total synthesis of (?)-cyathin A3, which is significant for the development of new pharmaceutical compounds.
Used in Enzyme Inhibition:
P-XYLOQUINONE is used as an inhibitor of jack bean urease, particularly in 50mM phosphate buffer at pH 7.0, for studying its effects on enzyme activity and potential applications in controlling enzymatic reactions.
Used in Chemical Research:
As a quinone derivative, P-XYLOQUINONE is utilized in chemical research to understand its properties, reactivity, and potential applications in the synthesis of various compounds and materials.

Synthesis Reference(s)

Synthetic Communications, 25, p. 1669, 1995 DOI: 10.1080/00397919508015851The Journal of Organic Chemistry, 53, p. 5453, 1988 DOI: 10.1021/jo00258a010

Purification Methods

Crystallise the quinone from EtOH. [Beilstein 7 IV 2090.]

InChI:InChI=1/C8H8O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3

Upstream product

• 95-87-4 2,5-Dimethylphenol 
• 615-90-7 2,5-dimethylhydroquinone 
• 95-78-3 2,5-Dimethylaniline 
• 137-17-7 2,4,5-trimethylaniline 
• 17696-37-6 2,5-dimethyl-4-(1,1-dimethylethyl)-phenol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 4682-53-5 12,13-epoxy-trichothec-9-ene-4,8-dione 
• 3096-64-8 N-(2,5-dimethylphenyl)hydroxylamine 
• 6393-01-7 2,5-Dimethyl-1,4-phenylenediamine 
• 3096-71-7 2,5-dimethyl-4-amino phenol 
• 917-64-6 methyl magnesium iodide 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 

Downstream Products

• 496-78-6 2,4,5-trimethylphenol 
• 488-70-0 2,3,4,5-tetramethylphenol 
• 14353-72-1 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one 
• 38770-37-5 2,5,5-trimethylcyclohexen-1,4-dion 
• 824427-15-8 (±)-(4aS*,5R*,8aS*)-5-methoxy-2,4a-dimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione 
• 856812-84-5 α-(4-hydroxy-2,5-dimethyl-phenoxy)-isobutyronitrile 
• 856813-22-4 α,α'-(2,5-dimethyl-p-phenylenedioxy)-di-isobutyronitrile 
• 615-90-7 2,5-dimethylhydroquinone 
• 2654-72-0 2,5-dihydroxy-3,6-dimethyl-1,4-benzoquinone 
• 2593-53-5 2,5-dimethyl-p-benzoquinone 4-oxime 
• 36164-92-8 2,5-dimethyl-p-benzoquinone dioxime 
• 22311-39-3 4-Hydroxy-2,5-dimethyl-phenoxyl 
• 28293-38-1 2,5-dibromo-3,6-dimethylcyclohexa-2,5-diene-1,4-dione 
• 502186-53-0 3-chloro-2,5-dimethyl-hydroquinone 

Relevant academic research and scientific papers

CPMAS 13C NMR Spectra of Quinones, Hydroquinones, and Their Complexes. Use of CMR To Follow a Reaction in the Solid State

CPMAS 13C NMR spectroscopy has been employed to follow the reaction at temperatures above 70 deg C of the crystalline 1/1 complex of 1,4-benzoquinone with 2,5-dimethyl-1,4-hydroquinone to give the 1/2 complex of 2,5-dimethyl-1,4-benzoquinone-hydroquinone and an equimolar amount of 2,5-dimethyl-1,4-benzoquinone.The redox reaction of a solid mixture of quinhydrone (1,4-benzoquinone-1,4-hydroquinone) with an equimolar amount of 2,5-dimethyl-1,4-hydroquinone gives the 1/2 complex of 2,5-dimethyl-1,4-benzoquinone with 1,4-hydroquinone with no evidence of formation of side products or accumulation of reaction intermediates.During preparation of a mixture of the 1/1 complex of 1,4-benzoquinone-2,5-dimethylhydroquinone with an equimolar amount of 1,4-hydroquinone the partial exchange of one hydroquinone for another in the complex occurs even during mixing of the components at room temperature.An equimolar mixture of 1,4-benzoquinones, 1,4-hydroquinone, and 2,5-dimethyl-1,4-hydroquinone underwent partial complexation at room temperature.These latter two mixtures when heated in the solid state each gave the 1/2 complex 2,5-dimethyl-1,4-benzoquinone-1,4-hydroquinone.As background for this work, CMR spectra of some crystalline quinones, hydroquinones, and their complexes (quinhydrones) have been obtained.The differences between the solid-state and corresponding solution spectra have been shown to be primarily in the multiplicities of some resonances but not others.It is suggested that a primary source of multiplicities in the quinones is CH---O interactions of the sort discussed by others in the analysis of the crystal packing patterns of such compounds.

A CONVENIENT SYNTHESIS OF ALKYL-SUBSTITUTED p-BENZOQUINONES FROM PHENOLS BY A H2O2/HETEROPOLYACID SYSTEM

Alkyl-substituted p-benzoquinones were easily synthesized in good yields by the oxidation of the corresponding phenols with a hydrogen peroxide/heteropolyacid couple in acetic acid

1,3-Dipolar Cycloreversion of the 1-Pyrazoline from 5-Diazo-10,11-dihydro-5H-dibenzocycloheptene and 2,5-Dimethyl-1,4-benzoquinone

Thermolysis of the pyrazoline formed from 5-diazo-10,11-dihydro-5H-dibenzocycloheptene and 2,5-dimethyl-1,4-benzoquinone gives the component diazoalkane and quinone via 1,3-dipolar cycloreversion, in competition with nitrogen extrusion to give the cyclopropane derivative.

Efficient oxidative coupling of 2,6-disubstituted phenol catalyzed by a dicopper(II) complex

Complexation of a rigid multi-pyridine ligand bis(2-pyridyl)-1,8- naphthyridine (bpnp) with [Cu2(TFA)4] (TFA = trifluoroacetate) resulted in the formation of a dinuclear copper(ii) complex, namely [Cu2(bpnp)(μ-OH)(TFA)3] (1). This complex has been characterized by X-ray crystallographic, spectroscopic and elemental analyses. Complex 1 is an efficient catalyst for the oxidative coupling of various 2,6-disubstituted phenols with molecular oxygen. Yields and selectivity depend on the reaction conditions employed, the best results being obtained in isopropanol or dioxane at 90 °C with yields of >99%. Mechanistic pathway of the catalysis is discussed.

Dimethyl sulfoxide and anhydrous copper (II) sulfate as alkylating reagent for 1,4-quinones

1,4-Quinones and its derivatives have been alkylated by dimethyl sulfoxide in the presence of anhydrous copper (II) sulfate at the active quinonoid position selectively, in a facile single step reaction with good yields.

Quinone tailored selective oxidation of methane over palladium catalyst with molecular oxygen as an oxidant

With the in situ generated H2O2 tailored by the addition of p-tetrachlorobenzoquinone, the product can be effectively steered towards either HCOOH or the methanol derivative CF3COOCH3 during the direct oxidation of methane with molecular oxygen over palladium catalyst.

Electrochemical oxidation of Δ9-tetrahydrocannabinol: a simple strategy for marijuana detection

Recently, it has been estimated that nearly 200 million people use marijuana with growing usage being attributed to the legalization and decriminalization of the drug around the world. A concerning implication of increased marijuana use is the alarming number of individuals who report driving under the influence of the drug, which has prompted the development of detection technologies. An electrochemical-based detection technology, akin to how the alcohol breathalyzer functions, would provide an attractive solution to this growing societal problem. The first step toward this goal is to develop a reaction that converts Δ9-tetrahydrocannabinol (Δ9-THC), the primary psychoactive substance in marijuana, to a derivative with diagnostic spectroscopic changes. We report the development of a mild electrochemical method for the oxidation of Δ9-THC to its corresponding p-quinone isomer. The photophysical and electrochemical properties of the resultant quinone show a dramatic shift in comparison to Δ9-THC. This simple protocol provides the foundation for the development of an electrochemical-based marijuana breathalyzer.

Efficient Metal-Free Catalytic Reaction Pathway for Selective Oxidation of Substituted Phenols

Selective oxidation of substituted phenols to p-benzoquinones is known to be inefficient because of the competing C-O coupling reaction caused by phenoxy radicals. The poor stability of conventional metal-based catalysts represents another bottleneck for industrial application. Here, we describe a metal-free reaction pathway in which onion-like carbon (OLC) as a low-cost catalyst exhibits excellent catalytic activity and stability in the selective oxidation of mono-, di- and trisubstituted phenols to their corresponding p-benzoquinones, even better than the reported metal-based catalysts (e.g., yield, stability) and industrial catalysts for particular substrates. Together with XPS, Raman, DFT calculations, and a series of comparative experiments, we demonstrate that the zigzag configuration as a type of carbon defects may play a crucial role in these reactions by stabilizing the intermediate phenoxy radicals.

Polyoxometalate-based supramolecular porous frameworks with dual-active centers towards highly efficient synthesis of functionalized: P -benzoquinones

Selective oxidation of substituted phenols is an ideal method for preparing functionalized p-benzoquinones (p-BQs), which serve as versatile raw materials for the synthesis of a variety of biologically active compounds. Herein, two new polyoxometalate-based supramolecular porous frameworks, K3(H2O)4[Cu(tza)2(H2O)]2[Cu(Htza)2(H2O)2][BW12O40]·6H2O (1) and H3K3(H2O)3[Cu(Htza)2(H2O)]3[SiW12O44]·14H2O (2) (Htza = tetrazol-1-ylacetic acid), were synthesized and structurally characterized by elemental analysis, infrared spectroscopy, thermal analysis, UV-vis diffuse reflectance spectroscopy, and single-crystal X-ray and powder diffraction. The single-crystal X-ray diffraction analysis indicates that both compounds possess unique petal-like twelve-nucleated Cu-organic units composed of triangular and hexagonal metal-organic loops. In 1, the Cu-organic units are isolated and [BW12O40]5- polyoxoanions are sandwiched between staggered adjacent triangular channels in the structure. However in 2, the Cu-organic units extend into a two-dimensional layered structure, and the [SiW12O44]12- polyoxoanions occupy the larger hexagonal channels in the stacked structure. Both compounds as heterogeneous catalysts can catalyze the selective oxidation of substituted phenols to high value-added p-BQs under mild conditions (60 °C) with TBHP as the oxidant, particularly in the oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-p-benzoquinone (TMBQ, key intermediate in vitamin E production). Within 8-10 min, the yield of TMBQ is close to 100%, and oxidant utilization efficiency is up to 94.2% for 1 and 90.9% for 2. The turnover frequencies of 1 and 2 are as high as 5000 and 4000 h-1, respectively. No obvious decrease in the yield of TMBQ was observed after five cycles, which indicates the excellent sustainability of both compounds. Our study of the catalytic mechanism suggests that there is a two-site synergetic effect: (i) the copper ion acts as the catalytic site of the homolytic radical pathway; and (ii) the polyoxoanion acts as the active center of the heterolytic oxygen atom transfer pathway. This journal is

Organophotocatalytic Aerobic Oxygenation of Phenols in a Visible-Light Continuous-Flow Photoreactor

A mild photocatalytic phenol oxygenation enabled by a continuous-flow photoreactor using visible light and pressurized air is described herein. Products for wide-ranging applications, including the synthesis of vitamins, were obtained in high yields by precisely controlling principal process parameters. The reactor design permits low organophotocatalyst loadings to generate singlet oxygen. It is anticipated that the efficient aerobic phenol oxygenation to benzoquinones and p-quinols contributes to sustainable synthesis.