22360-86-7

Basic information

• Product Name: 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE
• Synonyms: 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE;Dichloronitronaphthoquinone;2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE 97+%;5-Nitro-2,3-dichloro-1,4-naphthoquinone
• CAS NO: 22360-86-7
• Molecular Formula: C₁₀H₃Cl₂NO₄
• Molecular Weight: 272.04
• Mol File: 22360-86-7.mol

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 400.2 °C at 760 mmHg
• Flash Point: 195.9 °C
• Appearance: /
• Density: 1.71 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE(22360-86-7)
• EPA Substance Registry System: 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE(22360-86-7)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 22360-86-7(Hazardous Substances Data)

Usage

Uses

Used in Pesticide and Herbicide Industries:
2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE is used as a biocidal agent for controlling and eliminating unwanted plant and insect species. It operates by inhibiting the electron transport chain in the mitochondria of target organisms, disrupting cellular respiration and leading to their death. This makes it an effective tool in agricultural and horticultural practices to protect crops and maintain ecological balance.
Used in Dye Manufacturing:
In the dye industry, 2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE is utilized as an intermediate in the synthesis of various dyes. Its unique chemical structure contributes to the development of dyes with specific color properties and stability, catering to the diverse needs of textile, printing, and other industries that rely on colorants.
Used in Pharmaceutical Production:
2,3-DICHLORO-5-NITRO-1,4-NAPHTHOQUINONE also finds application in the pharmaceutical sector, where it serves as a precursor in the synthesis of certain drugs. Its chemical properties allow for the creation of compounds with potential therapeutic effects, contributing to the development of new medications and treatments.

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 856209-94-4 2,3,4-trichloro-4,5-dinitro-4H-naphthalen-1-one 
• 7664-93-9 sulfuric acid 
• 856210-03-2 2,2,3,3,4-pentachloro-5-nitro-3,4-dihydro-2H-naphthalen-1-one 
• 856211-71-7 2,3,4-trichloro-5-nitro-[1]naphthol 
• 3272-91-1 5-nitro-[1]naphthylamine 
• 17788-47-5 5-nitro-1,4-naphthoquinone 
• 64-19-7 acetic acid 

Downstream Products

• 22360-48-1 2-anilino-3-chloro-8-nitro-1,4-naphthoquinone 
• 22360-89-0 2-anilino-3-chloro-5-nitro-1,4-naphthoquinone 
• 1204290-55-0 4-(3-chloro-5-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)benzenesulfonamide 
• 1204290-56-1 4-(3-chloro-8-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)-N-(pyridin-2-yl)benzenesulfonamide 
• 1301627-27-9 N-(3-chloro-5-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-26-8 N-(3-chloro-8-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1610042-81-3 N-(8-amino-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-31-5 N-(8-amino-3-(3,5-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-32-6 N-(5-amino-3-(3,5-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1610042-78-8 N-(8-nitro-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-28-0 N-(3-(3,5-dimethylphenylamino)-8-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 1301627-29-1 N-(3-(3,5-dimethylphenylamino)-5-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide 
• 124289-79-8 9-(toluene-4-sulfonylamino)-dinaphtho[2,1-b;2',3'-d]furan-8,13-quinone 
• 109663-25-4 4-Amino-6-anilino-11-aza-5H-benzo<6,5-a>phenoxazin-5-one 

Relevant articles and documents

Activity-Based Probes for Isoenzyme- and Site-Specific Functional Characterization of Glutathione S-Transferases

Glutathione S-transferases (GSTs) comprise a diverse family of phase II drug metabolizing enzymes whose shared function is the conjugation of reduced glutathione (GSH) to endo- and xenobiotics. Although the conglomerate activity of these enzymes can be measured, the isoform-specific contribution to the metabolism of xenobiotics in complex biological samples has not been possible. We have developed two activity-based probes (ABPs) that characterize active GSTs in mammalian tissues. The GST active site is composed of a GSH binding "G site" and a substrate binding "H site". Therefore, we developed (1) a GSH-based photoaffinity probe (GSTABP-G) to target the "G site", and (2) an ABP designed to mimic a substrate molecule and have "H site" activity (GSTABP-H). The GSTABP-G features a photoreactive moiety for UV-induced covalent binding to GSTs and GSH-binding enzymes. The GSTABP-H is a derivative of a known mechanism-based GST inhibitor that binds within the active site and inhibits GST activity. Validation of probe targets and "G" and "H" site specificity was carried out using a series of competition experiments in the liver. Herein, we present robust tools for the characterization of enzyme- and active site-specific GST activity in mammalian model systems.

Electron donor-acceptor complexes of 2,3-dichloro-5-nitro-1,4- naphthoquinone with some methyl substituted anilines: Formation of 1:2 (A:D) complexes

The donor-acceptor complexes between 2,3-dichloro-5-nitro-1,4- naphthoquinone (DClNNQ) and some methyl substituted anilines were investigated by spectrophotometric method. This investigation was carried out in three different chlorinated solvents viz., chloroform, dichloromethane and 1,2-dichloroethane. Experimental evidences shows the formation of 1:2 (A:D) complexes but not 1:1 complexes. The calculated values of the oscillator strength and transition moment confirms this suggestion. The stoichiometry of the complexes was unaffected by the variation of temperature over a small interval and also change in solvent. The thermodynamic and spectroscopic parameters were evaluated in all the three solvents for the formation of CT-complexes. The influence of used solvents on the thermodynamic and spectroscopic parameters was investigated. The strength of the donors was also investigated.

Identification of compounds for the treatment or prevention of proliferative diseases

The invention features compounds for the treatment of cancer and other proliferative diseases. These compounds were identified in screening assays that contact candidate compounds with a cell containing a nucleic acid that includes a HER2 regulatory element and a reporter sequence. The invention further features compounds structurally related to those identified by the screening assays. Finally, the invention features methods of treating or preventing a proliferative disease using the compounds of the invention.

Spectrophotometric Studies of Electron-Donor-Acceptor Equilibria: The Presence of Bi- and Ter-Molecular Complexes

The donor-acceptor equilibria involving 2,3-dichloro-5-nitro-1,4-naphthoquinone (DClNNQ) and several substituted aromatic amines have been investigated spectrophotometrically in dichloromethane solution.Experimental evidence shows that they do not give 1 : 1 complexes alone.The results can be explained on the basis of the formation of termolecular complexes, in addition to 1 : 1 complexes.The formation constants for both 1 : 1 and 1 : 2 (A : D) complexes and their molar adsorptivities have been evaluated by using a multiparametric least squares computer program.

Topical Nonsteroidal Antipsoriatic Agents. 1. 1,2,3,4-Tetraoxygenated Naphthalene Derivatives

On the basis of previous observations that both 2,3-dihydro-2,2,3,3-tetrahydroxy-1,4-naphthoquinone (oxoline, 1) and 6-chloroisonaphthazarin (2) had demonstrated antipsoriatic activity in vivo, a series of structural derivatives of 2 were prepared and examined in the Scholtz-Dumas topical psoriasis bioassay.Of these six (5, 6, 9a, 10, 11a, 11b), the most effective compound was found to be 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene (RS-43179,lonapalene, 11a).An extensive series of 1,2,3,4-tetraoxygenated naphthalenes (16-74) incorporating variations of the ester, eth er and aryl substituents were prepared as analogues of 11a to examine the structural requirements for activity and were screened in vivo as inhibitors of arachidonic acid induced mouse ear edema, a topical bioassay capable of detecting 5-lipoxygenase inhibitors.Net lipophilicity, hydrolytic stability, and ring substitution play significant roles in determining the observed in vivo activity.Lonapalene (11a) is currently in clinical development as a topical applied nonsteroidal antipsoriatic agent.