1709-63-3

Basic information

• Product Name: 1,4,9,10-Anthracenetetrone
• Synonyms: 1,4,9,10-Anthracenetetrone;Quinizarinquinone;1,4,9,10-ANTHRACENETETRAONE
• CAS NO: 1709-63-3
• Molecular Formula: C₁₄H₆O₄
• Molecular Weight: 238.195
• Mol File: 1709-63-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 185 °C (sublm)
• Boiling Point: 421.3°Cat760mmHg
• Flash Point: 179.3°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 2.63E-07mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: 1,4,9,10-Anthracenetetrone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,9,10-Anthracenetetrone(1709-63-3)
• EPA Substance Registry System: 1,4,9,10-Anthracenetetrone(1709-63-3)

Safety Data

• Hazardous Substances Data: 1709-63-3(Hazardous Substances Data)

Usage

General Description

1,4,9,10-Anthracenetetrone, also known as anthraquinone, is a polycyclic aromatic ketone compound with the molecular formula C14H8O2. It is a yellow crystalline solid that is insoluble in water and most organic solvents. Anthraquinone is mainly used as an intermediate in the production of dyes, particularly red and violet dyes, and in the manufacturing of other organic compounds and pharmaceuticals. Additionally, it is used as a catalyst in the production of hydrogen peroxide and as a component in some electrolyte solutions for nickel-cadmium batteries. Anthraquinone is also known for its medicinal properties and has been used traditionally in Chinese and Ayurvedic medicine for its laxative and anti-inflammatory effects. However, its use in medicinal applications is limited due to its potential toxicity and side effects.

InChI:InChI=1/C14H6O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6H

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 5327-72-0 1,4-diamino-anthracene-9,10-diol 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 7664-93-9 sulfuric acid 
• 82-42-8 4-chloro-1-hydroxyanthraquinone 
• 13460-50-9 metaboric acid 
• 602-25-5 1,4-dichloroanthraquinone 
• 91318-51-3 anthracene-1,4,9,10-tetraone; radical anion 
• 6937-74-2 1-amino-4-nitroanthraquinone 
• 6416-55-3 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 

Downstream Products

• 3177-06-8 1,4-dihydroxy-2-phenylsulfanyl-anthraquinone 
• 882-33-7 diphenyldisulfane 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 63229-39-0 2-acetoxy-1,4,4a,12a-tetrahydronaphthacene-5,6,11,12-tetrone 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 890085-53-7 ethyl 3-(4-chlorophenyl)-3,3a,6,12-tetrahydro-3a,7-dihydroxy-2-methyl-6,12-dioxo-naphtho[2,3-d]indole-1-carboxylate 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 
• 58976-89-9 1,4-dihydro-5,12-dimethoxynaphthacene-6,11-dione 
• 58977-08-5 1,2,3,4-tetrahydro-2,5,12-trihydroxynaphthacene-6,11-dione 

Relevant articles and documents

A simple and efficient synthesis of optically active (+)-4-demethoxydaunomycinone

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Electrochemical and spectral study of the redox behavior and cardiotoxicity of anticancer drugs with antraquinone structure: Quinizarin

1,4-dihydroxyanthraquinone (quinizarin) is the simplest molecule, which represents the structure of the specific chromophore for some biological and pharmaceutical compounds, being the main part in the chemical structure of daunorubicin, doxorubicin, and mitoxantrone. The present paper investigates the behavior in reduction and oxidation processes of quinizarin in aprotic neutral and basic media by coupled electrochemical and spectral techniques (in-situ techniques), including absorption spectroscopy, in order to identify the intermediate species and to propose a reaction mechanism. The influence of electrogenerated bases (EGB) was investigated by comparison with the spectroelectrochemistry in presence of added tetrabutylammonium hydroxide (TBOH). The proposed reaction sequences are supported by Digisim 3.03 simulations. Semiempirical MO-calculations were performed to determine the electronic structural features implied in reduction and oxidation processes and to analyze the energetics of the electron transfer (ET) from different reduction intermediates to molecular oxygen.

1H and 13C NMR studies of some anthraquinones and anthracenetetrones

1H and 13C NMR chemical shifts are reported and assigned for 1,4,9,10- and 2,3,9,10-anthracenetetrone. In addition, NMR data are given for 2,3-dihydroxy-9, 10-anthraquinone, 2,3-dimethoxy-9,10-anthraquinone and 1-hydroxy-2-acetoxy-9,10-anthraquinone, encountered during the preparation of the anthracenetetrones.

Enthalpies of combustion of 1,4-naphthoquinone, 9,10-anthraquinone, 9,10-phenanthraquinone, 1,4,9,10-anthradiquinone, 5,8-dihydroxy-1,4-naphthoquinone, and 1,4-dihydroxy-9,10-anthraquinone

The standard (p0 = 0.1 MPa) molar enthalpies of combustion in oxygen at 298.15 K were measured by static-bomb calorimetry for some quinones and dihydroxyquinones.The standard molar enthalpies of sublimation at 298.15 K were measured by microcalorimetry for 1,4-naphthoquinone and 9,10-phenanthraquinone; values were selected from the literature for the remaining compounds in order to derive the standard molar enthalpies of formation in the gaseous state. The energies of the intramolecular hydrogen bonds in the dihydroxyquinones were assessed as (25 +/- 3) kJ*mol-1. 1,4,9,10-Anthradiquinone is apparently considerably strained, and although its reaction with water produces 1,4-dihydroxy-9,10-anthraquinone, a concomitant formation of hydrogen peroxide is shown to be thermodynamically improbable.