475-38-7

Basic information

• Product Name: 5,8-Dihydroxy-1,4-naphthoquinone
• Synonyms: ,8-Dihydroxy-[1,4]naphthoquinone;,8-Dihydroxy-1,4-naphthalenedione;1,4-Naphthoquinone, 5,8-dihydroxy-;2,3-Dihydro-1,4,5,8-naphthalenetetrone;5,8-dihydroxy-4-naphthalenedione;5,8-dihydroxy-4-naphthoquinone;5,8-Dihydroxynaphthoquinone;Naphthazarine
• CAS NO: 475-38-7
• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.15
• EINECS: 207-495-4
• Product Categories: API intermediates
• Mol File: 475-38-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 220-230 °C(lit.)
• Boiling Point: 285.64°C (rough estimate)
• Flash Point: 269.2 °C
• Appearance: dark purple to brown-black powder
• Density: 1.3366 (rough estimate)
• Vapor Pressure: 1.51E-10mmHg at 25°C
• Refractive Index: 1.5280 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.98±0.20(Predicted)
• Water Solubility: Soluble in water (5520 mg/L 25.).
• BRN: 880561
• CAS DataBase Reference: 5,8-Dihydroxy-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-Dihydroxy-1,4-naphthoquinone(475-38-7)
• EPA Substance Registry System: 5,8-Dihydroxy-1,4-naphthoquinone(475-38-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• RTECS: QL7970000
• Hazardous Substances Data: 475-38-7(Hazardous Substances Data)

Usage

Description

5,8-Dihydroxy-1,4-naphthoquinone is a naphthoquinone derivative in which the hydrogens at positions 5 and 8 are replaced by hydroxy groups. It is a dark purple to brown-black powder that exhibits unique chemical properties and solubility characteristics.

Uses

Used in Dye Industry:
5,8-Dihydroxy-1,4-naphthoquinone is used as a dyestuff for its ability to produce various shades of color in different solvents. It is soluble in water for a red light brown, soluble in ethanol for yellow brown, and exhibits green fluorescence. When added to a dye aqueous solution and treated with sodium hydroxide, the color changes to red, and upon air oxidation, it turns blue.
Used in Textile Industry:
In the textile industry, 5,8-Dihydroxy-1,4-naphthoquinone is used as a colorant and is valued for its fastness properties. It has been tested and meets the following standards:
Ironing Fastness: ISO 5
Light Fastness: ISO 6
Fulling: ISO 5
Perspiration Fastness: ISO 4
Soaping: ISO 5
Water: ISO 5
Alkali: ISO 5
Acid: ISO 5
These properties make it suitable for use in various textile applications where colorfastness and resistance to different conditions are essential.

Preparation

1,8-Dinitronaphthalene and 1,5-Dinitronaphthalene mixture or both alone and one of sulfur 40% fuming sulfuric ACID reaction, the product (5, 8 – dihydroxy – naphthoquinone) into Sulfurous acid?hydrogen salt.

Standard

Ironing Fastness

Alkali

Acid

ISO

5

Purification Methods

It crystallises in red-brown needles with a green shine from EtOH. It also crystallises from hexane and is further purified by sublimation at 2-10mm. [Huppert et al. J Phys Chem 89 5811 1985.] It is sparingly soluble in H2O but soluble in alkalis. The diacetate forms golden yellow prisms from CHCl3, m 192-193o and the 5,8-dimethoxy derivative has m 157o (155o) (from pet ether) [Bruce & Thompson J Chem Soc 1089 1955, IR: Schmand & Boldt J Am Chem Soc 97 447 1975, NMR: Brockmann & Zeeck Chem Ber 101 4221 1968]. The monothiosemicarbazone has m 168o(dec) from EtOH [Gardner et al. J Am Chem Soc 74 2106 1952]. [Beilstein 8 H 412, 8 III 3600.]

InChI:InChI=1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H

Upstream product

• 108-31-6 maleic anhydride 
• 123-31-9 hydroquinone 
• 108-30-5 succinic acid anhydride 
• 64-17-5 ethanol 
• 23077-93-2 1,4,5,8-naphthalenediquinone 
• 14569-45-0 5,8-diacetoxy-1,4-naphthoquinone 
• 5690-27-7 1,4,5,8-Tetrahydroxynaphthalene 
• 858023-98-0 2,3-dichloro-1,2,3,4,5,8-hexahydro-naphthalene-1,4,5,8-tetraone 
• 64-19-7 acetic acid 
• 605-71-0 1,5-dinitronaphthalene 
• 4793-98-0 1,4,5,8-tetranitronaphthalene 
• 615-67-8 chloro-p-hydroquinone 
• 150-78-7 1,4-dimethoxybezene 
• 2395-96-2 9-methoxyanthracene 

Downstream Products

• 14569-45-0 5,8-diacetoxy-1,4-naphthoquinone 
• 6047-49-0 1,4,5,8-Tetraacetoxy-naphthalin 
• 3057-02-1 1,4-Dihydroxy-6,7-dimethyl-5,8,8a,10a-tetrahydro-9,10-anthrachinon 
• 47123-72-8 2-phenylamino-5,8-dihydroxy-1,4-naphthoquinone 
• 15013-16-8 5,8-dimethoxynaphthoquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 4923-54-0 5,7-dihydroxy-1,4-naphthoquinone 
• 3786-46-7 3,6-dihydroxyphthalic acid 
• 4988-51-6 5,8-dihydroxy-2,3-dihydro-[1,4]naphthoquinone 
• 2961-04-8 1,4,5-trihydroxy-9,10-anthracenedione 
• 14597-06-9 5-acetoxy-8-hydroxy-1,4-naphthoquinone 
• 71639-99-1 5-(2',4'-dimethoxy-6'-methylbenzoyloxy)-8-hydroxy-1,4-naphthoquinone 
• 132632-70-3 4-(1-Cyclohexyl-ethoxy)-5,8-dihydroxy-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 
• 132632-77-0 5,8-Dihydroxy-4-(2-phenyl-propoxy)-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione 

Relevant articles and documents

A versatile synthesis of the 1,4-dihydroxynaphthoquinone nucleus

The electrochemical oxidation of different methoxynaphthalenes to afford the corresponding 5,8-dihydroxy-1,4-naphthoquinones has been examined. This method constitutes a new alternative and efficient route for the synthesis of the 5,8-dihydroxy-1,4-naphthoquinone nucleus. (C) 2000 Elsevier Science Ltd.

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.

Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents

Ruthenium-catalysis enabled the C-5 selective C-H oxygenation of naphthoquinones, and also sets the stage for the site-selective introduction of a hydroxyl group into anthraquinones. A-ring modified naphthoquinoidal compounds represent an important class of bioactive quinones for which the present study encompasses the first C-H oxygenation strategy by weak O-coordination.

Method for synthesizing 5,8-dihydroxy-1,4-naphthoquinone with molten salt method

The invention discloses a method for synthesizing 5,8-dihydroxy-1,4-naphthoquinone with a molten salt method. The method comprises the following main steps: step 1, a complex of 5,8-dihydroxy-1,4-naphthoquinone and AlCl3 is formed from hydroquinone and maleic anhydride as raw materials for synthesizing 5,8-dihydroxy-1,4-naphthoquinone as well as anhydrous AlCl3 as a catalyst and NaCl as molten salt through Friedel-Crafts acylation at high temperature and high pressure; step 2, free 5,8-dihydroxy-1,4-naphthoquinone is prepared from the complex of 5,8-dihydroxy-1,4-naphthoquinone and AlCl3 by digesting and then purified, and a 5,8-dihydroxy-1,4-naphthoquinone product is obtained. According to the method, the target product is obtained directly with one-step reaction on the basis of the molten salt method without an intermediate, so that the synthetic route is shortened greatly, aftertreatment is simple, a recrystallization step can be omitted, and extraction purity is guaranteed.