24929-02-0

Basic information

• Product Name: 1-amino-9,10-dihydro-4-hydroxy-9,10-dioxoanthracene-2-sulphonic acid
• Synonyms: 1-amino-9,10-dihydro-4-hydroxy-9,10-dioxoanthracene-2-sulphonic acid;1-Amino-4-hydroxy-9,10-dihydro-9,10-dioxoanthracene-2-sulfonic acid;1-Amino-9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenesulfonic acid;Einecs 246-537-6
• CAS NO: 24929-02-0
• Molecular Formula: C₁₄H₉NO₆S
• Molecular Weight: 319.28936
• EINECS: 246-537-6
• Mol File: 24929-02-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.749g/cm³
• Refractive Index: 1.75
• CAS DataBase Reference: 1-amino-9,10-dihydro-4-hydroxy-9,10-dioxoanthracene-2-sulphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-9,10-dihydro-4-hydroxy-9,10-dioxoanthracene-2-sulphonic acid(24929-02-0)
• EPA Substance Registry System: 1-amino-9,10-dihydro-4-hydroxy-9,10-dioxoanthracene-2-sulphonic acid(24929-02-0)

Safety Data

• Hazardous Substances Data: 24929-02-0(Hazardous Substances Data)

Usage

Derivative of

Anthraquinone

Functional groups

a. Hydroxy group
b. Keto group
c. Amino group
d. Sulphonic acid group

Use as a pH indicator

Yes

Color in acidic conditions

Orange to red

Color in alkaline conditions

Yellow to green

Applications

a. Dyeing and textile industry
b. Biochemical research
c. Medical research

InChI:InChI=1/C14H9NO6S/c15-12-9(22(19,20)21)5-8(16)10-11(12)14(18)7-4-2-1-3-6(7)13(10)17/h1-5,16H,15H2,(H,19,20,21)

Upstream product

• 116-82-5 1-amino-2-bromo-4-hydroxyanthraquinone 
• 116-85-8 4-hydroxy-1-aminoanthraquinone 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 88-63-1 2,4-Diaminobenzenesulfonic acid 
• 98416-38-7 4,9-Diamino-1,10-dioxo-1,10-dihydro-anthracene-2-sulfonic acid; compound with ammonia 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 1003-03-8 Cyclopentamine 
• 75-31-0 isopropylamine 
• 617-89-0 furan-2-ylmethanamine 
• 4319-49-7 1-aminomorpholine 
• 83759-22-2 1-amino-4-hydroxyanthraquinone-3-sulfonic acid 

Downstream Products

• 38924-11-7 1-[4-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-phenyl]-3-phenyl-urea 
• 97404-77-8 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2,3-dicarbonitrile 

Relevant articles and documents

Synthesis and In Silico Study of 4-Substituted 1-Aminoanthraquinones

Abstract: Eight new 4-substituted 1-amino-9,10-anthraquinones containing a primary amino group were syn-the-sized by nucleophilic substitution of bromine in 1-amino-4-bromo-9,10-anthraquinones. 1-Amino-4-[2-(hy-droxy-ethyl)amino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid containing a biogenic amine fragment (2-aminoethanol) was converted into the corresponding 1-triazenyl derivatives. The structure of the synthesized compounds was determined on the basis of the LC/MS and 13C and 1H NMR data, and their drug likeness was estimated in silico. Compounds with a good drug likeness score were analyzed by DIGEP-Pred, their possible interactions with proteins were simulated using STRING, and their biological activity was interpreted using the Kyoto Encyclopedia of Genes and Genomes.

Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists

A library of anilinoanthraquinone derivatives was synthesized by parallel Ullmann coupling reaction of bromaminic acid with aniline derivatives in solution using a compact parallel synthesizer. The products were purified by HPLC and evaluated as antagonists at mouse and human P2Y2 receptors. 4-Phenylamino-substituted 1-amino-2-sulfoanthraquinones, for example, 1-amino-4-(2-methoxyphenyl)-2-sulfoanthraquinone (PSB-716), were potent P2Y2 antagonists with IC50 values in the low micromolar range.

Analytical studies on the oxidative degradation of the reactive textile dye Uniblue A

Oxidative degradation process of organic materials in wastewater is an area of significant current interest. In the case of commercial textile dyes, little is known about the structures of the actual products that can form once a dye has been submitted to oxidative conditions. Here, a product analysis approach was applied to identify some of the major early degradation products of Uniblue A (UBA) when reacted with peroxydisulfate (PDS). UBA is the vinyl sulfone form and major wastewater constituent of the commercial anthraquinone textile dye C.I. Reactive Blue 19. Using NMR, LC-MS, and Raman, four reaction products could be identified, and possible reaction pathways are discussed.Oxidative degradation process of organic materials in wastewater is an area of significant current interest. In the case of commercial textile dyes, little is known about the structures of the actual products that can form once a dye has been submitted to oxidative conditions. Here, a product analysis approach was applied to identify some of the major early degradation products of Uniblue A (UBA) when reacted with peroxydisulfate (PDS). UBA is the vinyl sulfone form and major wastewater constituent of the commercial anthraquinone textile dye C.I. Reactive Blue 19. Using NMR, LC-MS, and Raman, four reaction products could be identified, and possible reaction pathways are discussed.

MECHANISM OF THE ULLMANN CONDENSATION

It has been found that the condensation rate of 1-amino-4-bromoanthraquinone-2-sulphonic acid (I) with 1,3-diaminobenzene-4-sulphonic acid (II)giving 1-amino-4-(3'-amino-4'-sulphoanilino)anthraquinone-2-sulphonic acid (III) in media of NaHCO3 - CO2 and NaHCO3 - Na2CO3 with catalysis by CuI obeys the kinetic relation v = k, being controlled by the kinetic relation v = k2 in media of NaH2PO4 - Na2HPO4 buffers.The suggested reaction mechanism presumes formation of a bifunctional catalyst CuCO3 or Cu2PO4(1-) which splits off the proton and bromide anion from the reaction intermediate in the rate-limiting step.