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Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-Dibromo-1,4-naphthoquinone is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a valuable building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of 3-[3-(2-carboxy-ethylsulfanyl)-1,4-dioxo-1,4-dihydro-naphthalen-2-ylsulfanyl]-propionic acid:
In this application, 2,3-dibromo-1,4-naphthoquinone serves as a starting material for the synthesis of a specific organic compound, which may have potential uses in various industries, including pharmaceuticals and materials science.
Used in the Synthesis of NSC 95397:
NSC 95397 is a protein tyrosine phosphatase antagonist, and 2,3-dibromo-1,4-naphthoquinone plays a crucial role in its synthesis. 2,3-DIBROMO-1,4-NAPHTHOQUINONE may have potential applications in the study and treatment of various diseases, particularly those involving protein tyrosine phosphatases.
Used as an Acaricide:
2,3-Dibromo-1,4-naphthoquinone is also used as an acaricide, which is a chemical agent that helps control or eliminate mites and ticks. Its effectiveness in this application is attributed to its ability to disrupt the normal functioning of these parasites, thereby reducing their populations.
Used in Photochemical Reactions:
2,3-DIBROMO-1,4-NAPHTHOQUINONE can undergo photochemical reactions with other molecules, such as 2-methoxy-1-alkene, to yield derivatives of 2-(2-alkanonyl)-1,4-naphthoquinone. These reactions can lead to the formation of new compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C10H4Br2O2/c11-7-8(12)10(14)6-4-2-1-3-5(6)9(7)13/h1-4H

Upstream product

• 90-15-3 α-naphthol 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 605-69-6 1-hydroxy-2,4-dinitronaphthalene 
• 84-87-7 1-hydroxy-4-naphthalenesulfonate 
• 130-15-4 [1,4]naphthoquinone 
• 36942-42-4 N-(4-hydroxy-naphthalen-1-yl)-benzenesulfonamide 
• 92025-40-6 2-bromo-3-ethylthio-1,4-naphthoquinone 
• 146767-46-6 2,3-dibromo-1,4-dihydroxynaphthalene 
• 36062-30-3 N-p-tolylsulfonyl-1,4-naphthoquinone-4-imine 
• 139719-06-5 4-chloro-N-(4-hydroxynaphthalen-1-yl)benzenesulfonamide 
• 91065-28-0 7,9-dibromo-6-hydroxy-benzocyclohepten-5-one 
• 146463-29-8 N-(3-bromo-4-hydroxynaphthalen-1-yl)-4-methylbenzenesulfonamide 
• 7732-18-5 water 
• 7726-95-6 bromine 

Downstream Products

• 26037-62-7 2-Methylmercapto-3-brom-naphthochinon-1,4 
• 872801-02-0 2-(N-ethyl-anilino)-3-bromo-[1,4]naphthoquinone 
• 64505-93-7 2-bromo-3-(phenylamino)naphthalene-1,4-dione 
• 54988-91-9 5-phenylbenzanthracene-7,12-dione 
• 93403-92-0 2-bromo-3-(2,2-diphenylethenyl)-1,4-naphthoquinone 
• 93403-97-5 2a,8a-Dibromo-1,1-diphenyl-1,2,2a,8a-tetrahydro-cyclobuta[b]naphthalene-3,8-dione 
• 64747-11-1 4-phenylanthra<2.1-b>thiophene-6,11-dione 
• 75488-23-2 4-p-tolylanthra<2,1-b>thiophene-6,11-dione 
• 135979-35-0 3-Brom-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,4-naphthochinon 
• 120385-86-6 8-methyl-7-phenyl-2H-benzopyran-2-spiro-1'-(2',3'-dibromo-4'-oxo-1',4'-dihydronaphthalene) 
• 72853-70-4 5-m-Tolylbenzanthracene-7,12-dione 
• 72853-69-1 3-Methyl-5-phenylbenzanthracene-7,12-dione 
• 75488-27-6 4-phenylanthra<1,2-b>thiophene-6,11-dione 
• 75488-31-2 4-p-chlorophenylanthra<1,2-b>thiophene-6,11-dione 

Relevant academic research and scientific papers

A Suzuki Approach to Quinone-Based Diarylethene Photochromes

Diarylethene photochromes show promise for use in advanced organic electronic and photonic materials with burgeoning considerations for biological applications; however, these compounds typically require UV light for photoswitching in at least one direction, thus limiting their appeal. We here introduce a naphthoquinone-based diarylethene that switches between open and closed forms with visible light. The synthesis of this quinone diarylethene relies on Suzuki methodology, allowing for the inclusion of functional groups not otherwise accessible with current synthetic routes.

Artificial photosynthesis of methanol from carbon dioxide and water via a Nile red-embedded TiO2 photocathode

The conversion of carbon dioxide into useful chemicals is a prospective strategy for alleviating the greenhouse effect and the depletion of energy. Herein, we report an artificial photosynthetic system composed of a photoanode and a photocathode comprised of NRx@TiO2 functionalized with Nile red via covalent linkage or Pd/NRx@TiO2 with additional palladium nanoparticles. The new Nile red derivatives and organic-inorganic composite electrodes were steadily prepared and well characterized using NMR, HRMS, UV-vis, FTIR, TEM, XPS, XRD and SEM. Methanol and oxygen were the products that could be detected in the liquid and gas phase. The main active species in this artificial photosynthesis system were proven using EPR spectroscopy to be hydroxy radicals releasing O2 gas via H2O2. Moreover, the carbon source of methanol was validated using a 13CO2 labeling experiment; 18O2 was determined to come from H2O using GC-MS. The optimal photoelectrocatalytic CO2 reduction was carried out using Pd/NR2@TiO2 as the working electrode yielding methanol at a rate of 106 μM h?1 cm?2 with high light quantum efficiency (Φcell = 0.95).

Electrochemical synthesis of quinones and other derivatives in biphasic medium

Electrochemical synthesis of quinones has been attempted from phenols, 1,4-dihydroxybenzenes, 1,4-dihydroxynaphthalenes and related compounds using biphasic media. Excellent yields of quinones (98%) or brominated diols have been achieved with good current efficiency. Reuse of the electrolyte without any modification and quantitative conversion of substrate with theoretical amount of current are the advantages of this method.

Vicinal acetylenic derivatives of 2-amino-1,4-naphthoquinone as key precursors of heterocyclic quinones

The Pd-catalyzed reaction between 3-acetylamino-2-bromo-1,4-naphthoquinones and CuI acetylides prepared in situ gave 3-acetylamino-2-alkynyl-1, 4-naphthoquinones, which were transformed into benz[f]indole-4,9-dione and benzo[g]quinoline-5,10-dione derivatives.

Synthesis of benz[f]indole-4,9-diones via acetylenic derivatives of 1,4-naphthoquinone

A synthetic route to benz[f]indole-4,9-diones from 1,4-naphthoquinone is described. Effective methods for cross-coupling of 3-acetylamino-2-bromo-1,4-naphthoquinone with terminal acetylenes and cyclization of the resulting 3-acetylamino-2-alkynyl-1,4-naphthoquinones are developed.

Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone

Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. CSIRO 2008.

Synthesis of Polyhalogenated 2-Cyclohexane-1,4-dione Derivatives Containing Hydrogen at the sp3-Carbon Atoms from N-Arylsulfonyl-p-quinonimines and N,N'-Bis(arylsulfonyl)-p-quinonediimines

Chlorination and bromination of N-arylsulfonyl-1,4-benzo(naphtho)quinonimines, N,N'-bis(arylsulfonyl)-1,4-benzoquinonediimines, N-arylsulfonyl-4-aminophenols, and N-arylsulfonyl-4-aminonaphthols gave a number of stable polyhalogenated structures containing hydrogen at the sp3-hybridized carbon atoms. The chlorination and bromination schemes of N-arylsulfonyl-p-quinonimines are discussed.

CONDENSATION INDOLE/NAPHTHOQUINONE. SYNTHESE D'UNE NOUVELLE SERIE D'INDOLYL-1,4-NAPHTHOQUINONES

Addition of an indole, which does not have a group at the 3-position, to 1,4-naphthoquinone leads to the expected 2-(3-indolyl)-1,4-naphthoquinone.When the 1,4-naphthoquinone is substituted at the 2-position by an alkyl or aryl group, the 2-substituted 3-(3-indolyl)-1,4-naphthoquinone is easily formed.However, when the 2-substituent of the quinone is functional (OH, OMe, Cl, Br, NC5H10, S-C6H5), in addition to the new series of expected indolylnaphthoquinones, several by-products resulting from elimination of the 2-substituted and/or further reaction of these compounds are formed.The outcome at the reaction appears to be very sensitive to the experimental conditions.

Solid state redox chemistry of hydroquinones and quinones

Solid state ceric ammonium nitrate (CAN) oxidation of hydroquinones to the corresponding quinones, gives best results when operating with ultrasonic irradiation. Nitrogen dioxide plays a key role in these 'solid-solid' oxidations. The oxidation of hydroquinones to quinones can also be achieved in a unique 'solid-solid-solid' reaction, i.e., by using a limited amount of CAN in the presence of a full equivalent of a solid cooxidant such as KBrO3. Reduction of quinones with sodium dithionite in the solid state gives rise to the corresponding highly colored quinhydrones and, eventually, to hydroquinones.

BROMINATION OF 4-ARENESULFONAMIDOPHENOLS (OR 1-NAPHTHOLS) AND N-ARYLSULFONYL-1,4-BENZO(NAPHTHO)QUINON-4-IMINES

2,3,6-Tribromo-N-phenylsulfonyl-1,4-benzoquinon-4-imines are formed on bromination of 4-arenesulfonamidophenols and N-aryl-sulfonyl-1,4-benzoquinon-4-imines but 2-bromo-N-arylsulfonyl-1,4-naphthoquinon-4-imines are formed from 4-arenesulfonamido-1-naphthols and N-arylsulfonyl-1,4-naphthoquinon-4-imines.