13243-65-7

Basic information

• Product Name: 2,3-DIBROMO-1,4-NAPHTHOQUINONE
• Synonyms: 2,3-DIBROMO-1,4-NAPHTHOQUINONE;RARECHEM BW GC 0009;2,3-DibroMonaphthalene-1,4-dione;2,3-Dibromo-1,4-naphthoquinone 97%;2,3-dibromo-1,4-dihydronaphthalene-1,4-dione
• CAS NO: 13243-65-7
• Molecular Formula: C₁₀H₄Br₂O₂
• Molecular Weight: 315.95
• EINECS: 236-223-7
• Product Categories: C10;Carbonyl Compounds;Ketones
• Mol File: 13243-65-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 218-222 °C(lit.)
• Boiling Point: 338.6°Cat760mmHg
• Flash Point: 117.2°C
• Appearance: /
• Density: 2.145g/cm³
• Vapor Pressure: 9.73E-05mmHg at 25°C
• Refractive Index: 1.724
• CAS DataBase Reference: 2,3-DIBROMO-1,4-NAPHTHOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIBROMO-1,4-NAPHTHOQUINONE(13243-65-7)
• EPA Substance Registry System: 2,3-DIBROMO-1,4-NAPHTHOQUINONE(13243-65-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13243-65-7(Hazardous Substances Data)

Usage

Description

2,3-Dibromo-1,4-naphthoquinone is a 2,3-disubstituted 1,4-naphthoquinone that belongs to the plumbagin family of compounds. It is characterized by the presence of two bromine atoms at the 2nd and 3rd positions and exhibits unique chemical properties due to its naphthoquinone structure. This organic compound is known for its potential applications in various chemical and pharmaceutical processes.

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 
• 135979-35-0 3-Brom-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,4-naphthochinon 
• 62051-45-0 5-(4-Bromo-phenyl)-benzo[a]anthracene-7,12-dione 
• 62051-41-6 2-Bromo-5-phenyl-benzo[a]anthracene-7,12-dione 
• 92866-03-0 2-bromo-3-(4-hydroxyphenylamino)naphthalene-1,4-dione 
• 64505-88-0 2-Brom-3-(3-carboxy-anilino)-α-naphthochinon 
• 64505-95-9 2-Brom-3-(4-aethoxy-anilino)-α-naphthochinon 
• 94163-44-7 2-Brom-3-(4-sulfo-anilino)-α-naphthochinon 
• 97353-26-9 2-Brom-3-<4-(2-diethylamino-ethoxycarbonyl)-anilino>-α-naphthochinon 

Relevant articles and documents

-

-

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).

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.