82-24-6

Basic information

• Product Name: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci
• Synonyms: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci;1-amino-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylicacid;9,10-dihydro-1-amino-9,10-dioxo-2-anthracenecarboxylicaci;1-amino-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid;1-Aminoanthraquinone-2-Carboxylic Acid;1-Amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid;2-Anthracenecarboxylic acid, 1-amino-9,10-dihydro-9,10-dioxo-;2-Anthraquinonecarboxylic acid, 1-amino-
• CAS NO: 82-24-6
• Molecular Formula: C₁₅H₉NO₄
• Molecular Weight: 267.23626
• EINECS: 201-406-2
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 82-24-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 291°C
• Boiling Point: 410.42°C (rough estimate)
• Flash Point: 302.1°C
• Appearance: /
• Density: 1.2671 (rough estimate)
• Vapor Pressure: 4.22E-14mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(82-24-6)
• EPA Substance Registry System: 1-amino-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylicaci(82-24-6)

Safety Data

• Hazardous Substances Data: 82-24-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 528, 1976 DOI: 10.1055/s-1976-24108

Purification Methods

It is used for the detection of Al, Mg Cd, Zn, Mn, Cu, Hg, Fe, Co, Ni and Pb. The methyl ester gives red needles from AcOH, m 228o. The ethyl ester, m 198o, crystallises also as red needles from AcOH. [Locher & Fietz Helv Chim Acta 10 667 1927, Beilstein 14 II 419, 14 III 168.]

InChI:InChI=1/C15H9NO4/c16-12-10(15(19)20)6-5-9-11(12)14(18)8-4-2-1-3-7(8)13(9)17/h1-6H,16H2,(H,19,20)/p-1

Upstream product

• 128-67-6 1-nitroanthraquinone-2-carboxylic acid 
• 129-15-7 1-nitro-2-methylanthraquinone 
• 117-07-7 1-amino-2-chloro-9,10-anthraquinone 
• 13432-32-1 1-amino-2,4-dichloroanthraquinone 
• 500541-02-6 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carbaldehyde 
• 82-45-1 1-amino-9,10-anthracenedione 
• 24094-44-8 1-amino-2-hydroxymethyl-9,10-dioxo-9,10-dihydroanthracene 
• 108-88-3 toluene 
• 85-44-9 phthalic anhydride 
• 6338-00-7 1-chloro-2-dibromomethyl-anthraquinone 
• 92439-31-1 2-methylanthraquinone-1-sulfonic acid 
• 129-35-1 1-chloro-2-methylanthraquinone 
• 84-54-8 2-methylanthracene-9,10-dione 
• 3300-23-0 1-amino-2-bromoanthraquinone 

Downstream Products

• 4182-49-4 1-amino-N-cyclohexyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 75535-00-1 1-amino-N-(2-methoxyphenyl)-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 82-45-1 1-amino-9,10-anthracenedione 
• 138058-33-0 3-Phenyl-1H-naphtho<2,3-h>quinazoline-2,4,7,12-tetrone 
• 452083-29-3 (rac)-2-hydroxymethyl-1-(2',4'-dimethoxy-6'-hydroxyphenyl)-anthraquinone 

Relevant articles and documents

CHARACTERISTIC FEATURES OF THE REACTION OF 3(5)-AMINO-5(3)-METHYLPYRAZOLE WITH 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID

In the reaction of 3(5)-amino-5(3)-methylpyrazole with 1-nitroanthraquinone-2-carboxylic acid in sulfolane at 150 deg C, 2-methylpyrazolonaphthoquinazoline-5,10.13-trione is formed with an admixture of 1-aminoanthraquinone-2-carboxylic acid and 1-aminoanthraquinone.Under similar conditions, from 4-amino-1,5-dimethylpyrazole, only 1-(1,5-dimethyl-4-pyrazolylamino)anthraquinone-2-carboxylic acid is formed.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

TRANSFORMATIONS OF 1-AZIDO-2-ANTHRAQUINONECARBOXYLIC ACID AND ITS ESTERS

When heated in nonpolar solvents, 1-azido-2-alkoxycarbonylanthraquinones are converted into 3-alkoxycarbonylanthra-6-isoxazolones.The product from the thermolysis of 1-azido-2-anthraquinonecarboxylic acid is 1,3-dihydroanthraisoxazole-3,6,11-trione.