615-93-0

Usage

Uses

Used in Pharmaceutical Synthesis:
2,5-Dichlorobenzo-1,4-quinone is used as a starting material in the synthesis of asterriquinone D, a natural product with potential biological activities and therapeutic properties.
Used in Photoreactor Technology Research:
2,5-Dichlorobenzo-1,4-quinone serves as a model compound to study the utility of a novel photoreactor equipped with an LED (light-emitting diode) light source and a fiber-optic CCD (charge-coupled device) spectrophotometer. This research aims to improve the efficiency and effectiveness of photochemical reactions.
Used in Organic Synthesis:
2,5-Dichlorobenzo-1,4-quinone is used in the synthesis of 2,5-dichloro-3,6-bi(3-indolyl)-1,4-hydroquinone through a palladium-catalyzed reaction with indole. This process demonstrates the compound's potential as a versatile intermediate in the preparation of various organic molecules and pharmaceuticals.

Purification Methods

Recrystallise it twice from 95% EtOH to give yellow needles [Beck et al. J Am Chem Soc 108 4018 1986]. The dioxime has m 278o(dec). [Beilstein 7 H 632, 7 I 346, 7 II 580, 7 III 3376, 7 IV 2081.]

InChI:InChI=1/C6H2Cl2O2/c7-3-1-5(9)4(8)2-6(3)10/h1-2H

Upstream product

• 95-82-9 2,5 dichloroaniline 
• 64-17-5 ethanol 
• 89487-79-6 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 
• 2675-77-6 1,4-dichloro-2,5-dimethoxybenzene 
• 695-99-8 2-Chloro-1,4-benzoquinone 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 
• 88-50-6 1-amino-2,5-dichlorobenzene-4-sulphonic acid 
• 20103-09-7 2,5-dichloro-1,4-phenylenediamine 
• 50392-39-7 2,5-dichloro-4-aminophenol 
• 106-51-4 p-benzoquinone 
• 89-61-2 2,5-dichloronitrobenzene 
• 71-43-2 benzene 
• 636-30-6 2,4,5-trichloroaniline 
• 56-23-5 tetrachloromethane 

Downstream Products

• 73713-78-7 2,5-Dichlor-3,6-dimorpholin-p-benzochinon 
• 24909-17-9 2,5-dichloro-3,6-diphenyl-[1,4]benzoquinone 
• 87-87-6 2,3,5,6-tetrachlorobenzene-1,4-diol 
• 608-94-6 2,3,5-trichloro-1,4-hydroquinone 
• 2675-77-6 1,4-dichloro-2,5-dimethoxybenzene 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 
• 27728-25-2 2,5-dibromo-3,6-dichloro-[1,4]benzoquinone 
• 35421-04-6 2,5-dichloro-[1,4]benzoquinone monooxime 
• 477883-79-7 3-bromo-2,5-dichloro[1,4]benzoquinone 
• 118-75-2 chloranil 
• 71155-99-2 2,5-dichlorohydroquinone diacetate 
• 125635-87-2 2,3,5-trichlorohydroquinone diacetate 
• 5030-67-1 2,5-dianilino-3,6-dichloro-1,4-benzoquinone 
• 120024-73-9 hexa-P-phenyl-P,P'-(2,5-dichloro-p-phenylenedioxy)-di-phosphonium; (2-chloro-5-triphenylphosphonio-benzene-1,4-diolate)-chloride 

Relevant academic research and scientific papers

Estimation of kinetic parameters of reversible chain reactions of quinoneimines with hydroquinones having self-acceleration periods

A new approach is suggested for determining the kinetic parameters and rate constants of the elementary steps of reversible chain reactions having self-acceleration periods due to the long time required for the concentrations of the chain-carrier radicals to reach their steady-state values. This approach is illustrated by the example of the reversible chain reaction between N,N′-diphenyl-1,4-benzoquinonediimine and 2,5-dichlorohydroquinone in chlorobenzene. The disappearance rate of one of the initial reactants, N,N′-diphenyl-1,4-benzoquinonediimine, at the inflection point of its disappearance curve, is considered as the basic kinetic characteristic of the reaction. The empirical function y = aexp(bt c ) + d, where a, b, c, and d are the fitted parameters (b 1), is suggested for approximating the S-shaped kinetic curves and for calculating the reaction rate. The rate constants of the elementary steps are preferably derived from experimental data obtained at equal concentrations of the initial reactants, and also product additions when their effect on the reaction rate is studied. The effective rate constant of chain termination is derived from the time to reach the steady state. The results obtained in this way are compared with earlier data obtained using the "initial" reaction rates calculated by means of exponential approximation of portions of N,N′-diphenyl-1,4- benzoquinonediimine disappearance curves after the inflection point.

The impact of an isoreticular expansion strategy on the performance of iodine catalysts supported in multivariate zirconium and aluminum metal-organic frameworks

Iodine functionalized variants of DUT-5 (Al) and UiO-67 (Zr) were prepared as expanded-pore analogues of MIL-53 (Al) and UiO-67 (Zr). They were prepared using a combination of multivariate and isorecticular expansion strategies. Multivariate MOFs with a 25% iodine-containing linker was chosen to achieve an ideal balance between a high density of catalytic sites and sufficient space for efficient diffusion. Changes to the oxidation potential of the catalyst as a result of the pore-expansion strategy led to a decrease in activity with electron rich substrates. On the other hand, these larger frameworks proved to be more efficient catalysts for substrates with higher oxidation potentials. Recyclability tests for these larger MOFs showed sustained catalytic activity over multiple recycles.

Reactivity of a Ru(iii)-hydroxo complex in substrate oxidation in water

A mononuclear RuIII-OH complex oxidizes substrates such as hydroquinones in water through a pre-equilibrium process based on adduct formation by hydrogen bonding between the RuIII-OH complex and the substrates. The reaction mechanism switches from hydrogen atom transfer to electron transfer depending on the oxidation potential of substrates. This journal is

The use of sodium chlorate/hydrochloric acid mixtures as a novel and selective chlorination agent

Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the α-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.

Characterization of chlorophenol 4-monooxygenase (TftD) and NADH:FAD oxidoreductase (TftC) of burkholderia cepacia AC1100

Burkholderia cepacia AC1100 completely degrades 2,4,5-trichlorophenol, in which an FADH2-dependent monooxygenase (TftD) and an NADH:FAD oxidoreductase (TftC) catalyze the initial steps. TftD oxidizes 2,4,5-trichlorophenol (2,4,5-TCP) to 2,5-dichloro-p-benzoquinone, which is chemically reduced to 2,5-dichloro-p-hydroquinone (2,5-DiCHQ). Then, TftD oxidizes the latter to 5-chloro-2-hydroxy-p-benzoquinone. In those processes, TftC provides all the required FADH2. We have determined the crystal structures of dimeric TftC and tetrameric TftD at 2.0 and 2.5 A resolution, respectively. The structure of TftC was similar to those of related flavin reductases. The stacked nicotinamide:isoalloxazine rings in TftC and sequential reaction kinetics suggest that the reduced FAD leaves TftC after NADH oxidation. The structure of TftD was also similar to the known structures of FADH2-dependent monooxygenases. Its His-289 residue in the re-side of the isoalloxazine ring is within hydrogen bonding distance with a hydroxyl group of 2,5-Di-CHQ.AnH289Amutation resulted in the complete loss of activity toward 2,5-DiCHQ and a significant decrease in catalytic efficiency toward 2,4,5-TCP. Thus, His-289 plays different roles in the catalysis of 2,4,5-TCP and 2,5-DiCHQ. The results support that free FADH2 is generated by TftC, and TftD uses FADH2 to separately transform 2,4,5-TCP and 2,5-DiCHQ. Additional experimental data also support the diffusion of FADH2 between TftC and TftD without direct physical interaction between the two enzymes.

Synthesis of 2,5-Diaminoquinones by one-pot copper-catalyzed aerobic oxidation of hydroquinones and addition reaction of amines

The aerobic oxidation of various hydroquinones was achieved by using copper nanoparticles entrapped in aluminum oxyhydroxide [Cu/ AlO(OH)] at room temperature. Furthermore, 2,5diamino-1,4-benzoquinones were synthesized directly from hydroquinone and amines by a one-pot procedure consisting of the copper-catalyzed aerobic oxidation of hydroquinones and the double addition of amines to the resulting quinones.

Aerobic oxidation of hydroquinone derivatives catalyzed by polymer-incarcerated platinum catalyst

(Chemical Equation Presented) It's a lock-in! A remarkably wide substrate scope of hydroquinones are oxidized to quinones in high yields in a platinum-catalyzed process with as low as 0.05 mol% catalyst. The aerobic oxidation is catalyzed by platinum nanoclusters trapped in a styrene-based polymer network (see scheme, PI Pt=polymer-incarcerated nanoclusters). The catalyst could be reused at least 13 times without any loss of catalytic activity.

The mediatory activity of Ce(IV)/Ce(III) redox system immobilized in nafion film on glassy carbon

Properties of the glassy carbon modified with Ce(III) ions immobilized in Nafion film and the catalytic activity of these ions or the catalytic activity of the modified conducting phase in electrochemical oxidation of some hydroquinone, phenylenediamine and 4-hydroxybenzoic acid derivatives were investigated. The redox activity was characterized in aqueous solutions of perchloric acid by cyclic voltammetry. The redox process was diffusion-limited which can suggest that the cerium(III) ions immobilized in the Nafion multilayer was rate-controlling. The increase of anodic peaks of investigated compounds during oxidation on the modified electrode (GC/Nafion/Ce(III)), and drastic decrease of cathodic peak related to Ce(IV) ions reduction, points to the mediatory activity of these ions. The increase of oxidation currents observed during preparative electrolyses indicates the catalytic properties of the modified conducting phase. The preparative electro-oxidation of investigated compounds showed that the 100% conversion of the substrate occurs in the shortest time on glassy carbon modified with Ce(III) ions immobilized in Nafion film. AFM tapping mode phase imaging was used to identify the hydrophobic and hydrophilic regions of Nafion perfluorosulfonate cation exchange membranes. The clusters agglomerates have a range of sizes from 5 to 30 nm.

Rate constants of elementary steps of the reversible chain reaction of N-phenyl-1,4-benzoquinonemonoimine with 2,5-dichlorohydroquinone

The kinetics of reversible chain reactions in quinoneimine-hydroquinone systems has first been studied for the reaction of N-phenyl-1,4- benzoquinonemonoimine with 2,5-dichloro-hydroquinone used as an example. The dependences of the reaction rate on the concentration of the initial reactants, initiator, and each product were studied. The reliable estimates of the rate constants of 11 (of 12) elementary steps of this reaction were obtained from the experimental data using the earlier derived formulas and the method of equal concentrations developed in the present work.

Solvent effect on the equilibrium constant of the chain reversible reaction of N,N'-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone

The temperature dependences of the equilibrium constant K of the reversible chain reaction of N,N'-diphenyl-1,4-benzoquinonediimine with 2,5-dichlorohydroquinone in benzene, chlorobenzene, anisole, benzonitrile, and CCl4 were studied. The enthalpies and entropies of the reaction in these solvents were determined, and a linear dependence between them in aromatic solvents was found. The equilibrium constant depends on the solvent nature: the replacement of CCl4 by benzene at T = 298 K increases K from 13.6 to 140. The solvation effects are caused by several types of intermolecular interactions of participants of equilibrium with the medium. The decrease in K in the benzene-anisole-benzonitrile series is related, to a great extent, to complex formation with hydrogen bonding between 2,5-dichlorohydroquinone and the solvents. In anisole a charge-transfer complex is formed between the solvent and reaction product (2,5-dichloroquinone). The constant and enthalpy of the complexation were estimated.