14918-69-5

Basic information

• Product Name: 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE
• Synonyms: 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE;2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTOQUINONE;NA;RARECHEM AR PA 0036;2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTOQUINONE 95+%;2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPTHOQUINONE;2,3-Dichloro-5,8-dihydroxy-1,4-naphthoquinone ,95%;2,3-Dichloro-5,8-dihydroxy-1,4-naphthoquinone 95%
• CAS NO: 14918-69-5
• Molecular Formula: C₁₀H₄Cl₂O₄
• Molecular Weight: 259.04
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Alcohols;Monomers;Polymer Science
• Mol File: 14918-69-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 197-199 °C(lit.)
• Boiling Point: 366.21°C (rough estimate)
• Flash Point: 280.6 °C
• Appearance: dark purple powder
• Density: 1.5311 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5110 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.84±0.20(Predicted)
• CAS DataBase Reference: 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE(14918-69-5)
• EPA Substance Registry System: 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE(14918-69-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 14918-69-5(Hazardous Substances Data)

Usage

Chemical Properties

DARK PURPLE POWDER

InChI:InChI=1/C10H4Cl2O4/c11-7-8(12)10(16)6-4(14)2-1-3(13)5(6)9(7)15/h1-2,13-14H

Upstream product

• 108-31-6 maleic anhydride 
• 608-44-6 2,3-dichlorohydroquinone 
• 1122-17-4 dichloromaleic acid anhydride 
• 123-31-9 hydroquinone 
• 150-78-7 1,4-dimethoxybezene 
• 615-67-8 chloro-p-hydroquinone 
• 2100-42-7 2-chloro-1,4-dimethoxybenzene 
• 39542-66-0 2,3-dichlorohydroquinone dimethyl ether 
• 78456-63-0 2,3-dichloro-1,4,5,8-naphthodiquinone 
• 2395-96-2 9-methoxyanthracene 

Downstream Products

• 14918-66-2 5,8-dihydroxy-2-methoxy-[1,4]naphthoquinone 
• 3560-71-2 5,8-dihydroxy-2,3,6-trimethoxy-1,4-naphthoquinone 
• 118006-14-7 diacetato-de 2,3-dicloronaftazarina 
• 206255-36-9 2-Chloro-5,8-dihydroxy-3-phenoxy-[1,4]naphthoquinone 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 1143-11-9 2,3,5,6,8-pentahydroxynaphthalene-1,4-dione 
• 15013-16-8 5,8-dimethoxynaphthoquinone 
• 88818-28-4 1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde 
• 1247849-68-8 2,3-bis(phenylselanyl)-5,8-dihydroxynaphthoquinone 
• 84900-49-2 2-Anilino-3-amino-5,8-dihydroxy-1,4-naphthoquinone 
• 517-82-8 echinochrome A 
• 206255-33-6 2-Chloro-5,8-dihydroxy-3-(3-hydroxy-phenoxy)-[1,4]naphthoquinone 
• 206255-35-8 2-Chloro-3-(3,5-dimethoxy-phenoxy)-5,8-dihydroxy-[1,4]naphthoquinone 
• 206255-34-7 2-Chloro-5,8-dihydroxy-3-(3-methoxy-phenoxy)-[1,4]naphthoquinone 

Relevant articles and documents

A convenient synthesis of 2-formyl-1,8:4,5-bis(methylenedioxy) naphthalene

2,3-Dihydronaphazarin was prepared from 1,4-dimethoxybenzene and dichloromaleic anhydride. Reaction with bromochloromethane gave 1,8:4,5-bis(methylenedioxy)naphthalene which with NBS, gave 2-bromo-1,8:4,5-bis- (methylenedioxy)naphthalene. Reaction of the Grignard derivative with DMF afforded 2-formyl-1,8:4,5-bis(methylenedioxy)naphthalene. This method had several advantages compared with the reported synthesis, including fewer steps, milder condition and higher yields.

A hydrogen peroxide-activated Cu(II) pro-ionophore strategy for modifying naphthazarin as a promising anticancer agent with high selectivity for generating ROS in HepG2 cells over in L02 cells

Targeting redox vulnerability of cancer cells by pro-oxidants capable of generating reactive oxygen species (ROS) has surfaced as an important anticancer strategy. Due to the intrinsic narrow therapeutic window and other dangerous side effects of ROS generation, it is highly needed and challenging to develop pro-oxidative anticancer agents (PAAs) with high selectivity for generating ROS in cancer cells. Herein we report a hydrogen peroxide (H2O2)-activated Cu(II) pro-ionophore strategy to develop naphthazarin (Nap) as such type of PAAs based on the H2O2-mediated conversion of boronate to free phenol. The boronate-protected Nap (PNap) can exploit increased levels of H2O2 in HepG2 cells to in situ release Nap followed by its efflux via conjugation with reduced glutathione (GSH), allowing that the Nap-GSH adduct works as a Cu(II) ionophore to induce continuously GSH depletion via a reduction-dependent releasing of Cu(I) by GSH. This strategy endows PNap with the unprecedented ability to hit multi-redox characteristics (increased levels of H2O2, GSH and copper) of HepG2 cells, leading to ROS generation preferentially in HepG2 cells along with their selective death.

Discovery of 1,4-Naphthoquinones as a New Class of Antiproliferative Agents Targeting GPR55

A new series of 1,4-naphthoquinones, bearing various cyclic and aliphatic amines on C2, was designed and synthesized to identify antiproliferative agents for triple-negative breast cancer, which represents a clinical challenge without targeted therapies. Among naphthoquinones, 2a and 3a inhibited the proliferation of MDA-MB-231 cells (EC50 = 1.6 and 2.7 μM, respectively), compared to primary human breast cells MCF10A. Furthermore, they did not affect the viability of peripheral blood mononuclear cells (PBMC), suggesting their potential safer use for cancer treatment. Recently, correlations have emerged between the expression of G protein-coupled receptor 55 (GPR55) and both triple-negative breast cancer development and invasion, making it a promising target for the development of targeted therapies. Based on this evidence, molecular docking studies supported the hypothesis of binding to GPR55, and pharmacological tests suggested that compound 3a could exert its antiproliferative activity acting as a GPR55 inverse agonist.

PROTEIN KINASE INHIBITORS AND USE THEREOF FOR TREATMENT OF NEIMODEGENERATIVE DISEASES

The present disclosure relates to compounds that act as protein kinase inhibitors, especially CK1δ and/or CK1ε inhibitors, which can be used to treat a serine/threonine kinase-dependent disease and condition, such as neurodegenerative diseases like Alzheimer's Disease, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for neurodegenerative diseases, including Alzheimer's disease.

Synthesis of Spinochrome D, A Metabolite of Various Sea-Urchin Species

The sea-urchin metabolite spinochrome D (1) was synthesized in 58% overall yield via oxidation of 2,3-dichloronaphthazarin (13) into 2-hydroxy-6,7-dichloronaphthazarin (14), O-methylation of 14, nucleophilic substitution by MeO groups of the Cl atoms in the resulting 2-methoxy-6,7-dichloronaphthazarin (19), and hydrolysis of the obtained 2,3,6-trimethoxynaphthazarin (10).