7474-86-4

Usage

Chemical structure

2,3-dichloronaphthalene-1,4-diol is a chemical compound that contains two chlorine atoms and a hydroxyl group attached to a naphthalene ring.

Applications

It is commonly used in the synthesis of pharmaceuticals and agrochemicals.

Antibacterial and antifungal properties

2,3-dichloronaphthalene-1,4-diol is known for its antibacterial and antifungal properties, making it a potential candidate for the development of new drugs.

Potential use as a pesticide

It has been studied for its potential use as a pesticide.

Manufacturing of dyes and pigments

2,3-dichloronaphthalene-1,4-diol is also used in the manufacturing of dyes and pigments.

Toxicity

Due to its potential toxicity, proper handling and safety precautions should be taken when working with this chemical.

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 41245-34-5 1,4-Diacetoxy-2,3-dichlor-naphthalin 
• 41245-39-0 1,4-bis-benzoyloxy-2,3-dichloro-naphthalene 
• 1003853-52-8 1,2,3,4-tetrakis(4-methylphenyl)naphthalene 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 

Relevant academic research and scientific papers

Hydration effects on the triplet exciplex between 2,3-dihalo-1,4- naphthoquinone and furan studied by steady-state and laser flash photolyses

Photochemical interactions of triplet 2,3-dibromo- and 2,3-dichloro- 1,4-naphthoquinones (DBNQ and DCNQ) with furan in acetonitrile (ACN) and a mixture of ACN and water (4:1 v/v) were investigated by means of product analysis, steady-state and nanosecond laser flash photolysis. The photoproducts of DBNQ and DCNQ in the presence of furan in ACN were 2-bromo- and 2-chloro-3-(2-furyl)-1,4-naphthoquinones with the quantum yields for production (Φ(pro) of 0.12 and 0.05, respectively, whereas in aqueous ACN, 2,3-dibromo- and 2,3-dichloro-1,4-dihydroxynaphthalenes Φ(pro) = 0.12 and 0.17, respectively. By nanosecond laser photolysis at 355 nm, it was found that triplet DBNQ and DCNQ were quenched by furan with rate constants (k(q)) of 2.0 x 109 and 3.0 x 109 dm3 mol-1 s-1 in ACN and 6.1 x 109 and 6.4 x 109 dm3 mol s-1 in aqueous ACN, respectively. After depletion of triplet DBNQ and DCNQ, no transient absorption in the region 360-600 nm was observed in ACN while the corresponding anion radicals having molar absorption coefficients (ε(ani)) of 7700 and 7900 dm3 mol-1 cm-1 at 400 nm, respectively, were formed in aqueous ACN. The initial interaction of triplet DBNQ and DCNQ with furan in aqueous ACN was found to be electron transfer with efficiencies (α(et)) of 0.22 and 0.23, respectively, while that in ACN was presumed to be dominated by induced quenching. The deactivation mechanism of triplet DBNQ and DCNQ by furan was discussed from the viewpoint of the free energy changes (ΔG) for electron transfer. It was suggested that the triplet exciplex with weak charge-transfer character played an important role being controlled by the solvation energy in the ΔG term.

Synthesis, biological evaluation, molecular docking and structure-activity relationship studies of halogenated quinone and naphthoquinone derivatives

Protein glycation, oxidative stress and acetyl cholinesterase enzyme (AChE) are closely implicated in the pathogenesis of diabetic complications and Alzheimer's disease. In this study, we synthesized a series of previously unexplored molecular analogues of halogenated quinone and naphthoquinone to investigate their therapeutic potency against protein glycation, free radical production and acetyl cholinesterase enzyme. The study on protein glycation resulted in the identification of two novel antiglycation agents such as 2,3-dichloronaphthalene-1,4-bistriflate (3) and 2,3-dibromonaphthalene-1,4-bis (trifluoromethanesulfonate) (6) with IC50 values less than 16 micromolar range. Moreover, 2,3-dichloro-1,4- naphthoquinone (DCNQ) (1), 2,3-dibromonaphthoquinone (4), 2,3-dibromonaphthalene-1,4-diol (5) and 2,3,5,6-tetrachlorobenzene-1,4-bis(trifluoromethane- sulfonate) (8) exhibited potent antiglycation activity with IC50 values of 54 ± 1.02, 43 ± 0.5, 65 ± 1.00 and 60 ± 1.25 μM, respectively as compared to the standard inhibitor rutin with an IC50 value of 98 ± 1.50 μM. The structure-activity relationship (SAR) demonstrated that the presence of bis-(trifluoromethanesulfonate) as substituents alongwith halogens moieties appreciably influenced inhibitory potential and enhanced the antiglycation potential significantly. On free radical DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging assay, 2,3,5,6-tetrachlorobenzene-1,4-bis(trifluoromethane- sulfonate) (8), showed significant antioxidant activity with IC50 values 52 ± 1.50 μM. On acetyl cholinesterase inhibition assay, compound 8 and 2,3-dichloronaphthalene-1,4-bistriflate 3, exhibited considerable inhibition with IC50 values of 98 ± 1.00 μM and 124 ± 1.50 μM, respectively. The SAR studies against AChE revealed that the presence of chlorine and trifluoromethanesulfonate both combined together in a compound enhanced its inhibitory activity several folds. In support of experimental observations, molecular docking studies with the active site of acetyl cholinesterase also confirmed the stronger inhibition of compounds 3, and 8 compared to others derivatives. These inhibitors demonstrated hydrogen bonding with Tyr124 and π-π stacking with Tyr341 of the active site residues. In this study, galantamine, rutin and propyll gallate were used as standard inhibitors, respectively.

Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous-Flow Hydrogenation-Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts

Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi-Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous-flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous-flow conditions to afford the desired products in good to excellent yields. Especially, air-sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous-flow conditions without decomposition.

Diels-Alder trapping of in situ generated dienes from 3,4-dihydro-2H-pyran with p-quinone catalysed by p-toluenesulfonic acid

This comprehensive study portrays that p-toluenesulfonic acid is a more efficient catalyst for the reaction between p-quinones and 3,4-dihydro-2H-pyran, than the Lewis acids. The products were accomplished by the Diels-Alder cycloaddition reaction and their mechanistic pathways have been formulated. The impact of C2 and C2,5 substituents of the p-quinones on the cycloaddition reaction has been explored. Remarkably, it is the first report to explore this kind of in situ generated diene for the Diels-Alder cycloaddition reaction.

Palladium-catalyzed chemo- and regioselective cross-coupling reactions of 2,3-dichloronaphthalene-1,4-bistriflate Dedicated to Prof. Kimoon Kim

Palladium-catalyzed chemoselective and regioselective cross-coupling reactions of 2,3-dichloro-1,4-(trifluoromethanesulfonyloxy)naphthalene with aryl boronic acids selectively afforded a variety of mono-, di-, and tetraphenylnaphthalenes. These reactions

Chemistry of L-ascorbic acid. Part 3.1 Photoreduction of quinones with 5,6-O-isopropylidene-L-ascorbic acid

Upon irradiation with UV light, instead of undergoing the Paterno-Buechi reaction, 5,6-O-isopropyIidene-L-ascorbic acid reduced quinones quite efficiently and rapidly to the corresponding hydroquinones. The Royal Society of Chemistry 2000.

Tetrathiafulvalene quinones, hydroquinones and esters

Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of 8. Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.