145-48-2

Basic information

• Product Name: 1,4-Dihydroxyanthraquinone-2-sulfonic acid
• Synonyms: 9,10-dihydro-1,4-dihydroxy-9,10-dioxoanthracene-2-sulphonic acid;1,4-DIHYDROXYANTHRAQUINONE-2-SULFONIC ACID;RUFIANIC ACID;QUINIZARINSULFONIC ACID;2-Quinizarinsulfonic acid;9,10-Dihydro-1,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid;QUINIZARINSULPHONATE;1,4-Dihydroxy-2-sulfoanthraquinone
• CAS NO: 145-48-2
• Molecular Formula: C₁₄H₈O₇S
• Molecular Weight: 320.27
• EINECS: 205-654-2
• Mol File: 145-48-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.792g/cm³
• Refractive Index: 1.743
• PKA: -1.33±0.20(Predicted)
• CAS DataBase Reference: 1,4-Dihydroxyanthraquinone-2-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydroxyanthraquinone-2-sulfonic acid(145-48-2)
• EPA Substance Registry System: 1,4-Dihydroxyanthraquinone-2-sulfonic acid(145-48-2)

Safety Data

• Hazardous Substances Data: 145-48-2(Hazardous Substances Data)

Usage

General Description

1,4-Dihydroxyanthraquinone-2-sulfonic acid, also known as quinizarin, is a synthetic chemical compound with a molecular formula of C14H8O6S. It is a dark red crystalline powder that is soluble in water and has a wide range of applications in the chemical industry. Quinizarin is predominantly used as a dye and pigment in the production of inks, paints, and textile dyes. Additionally, it is used in the manufacturing of analytical reagents and as a colorimetric reagent for the determination of various metal ions. The compound has also been studied for its potential pharmacological properties, including its anti-cancer and anti-inflammatory effects, making it a subject of interest in the pharmaceutical and biomedical fields.

InChI:InChI=1/C14H8O7S/c15-8-5-9(22(19,20)21)14(18)11-10(8)12(16)6-3-1-2-4-7(6)13(11)17/h1-5,15,18H,(H,19,20,21)

Synthetic route

Reactive Blue 19 vinyl sulfone → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (24929-02-0) + 4-(3-ethenesulfonyl-phenylamino)-1-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid + 4-(3-ethenesulfonyl-phenylamino)-1-(3-ethenesulfonyl-phenylazo)-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid

Conditions	Yield
With dipotassium peroxodisulfate In water at 65℃; for 7h; pH=3.0 - 5.5; Product distribution;	A 5% B n/a C 40% D 8%

1,4-dihydroxy-9,10-anthracenedione (81-64-1) → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2)

Conditions	Yield
With manganese(IV) oxide; water; sodium sulfite
With manganese(IV) oxide; potassium sulfite; water
With water; copper(II) oxide; sodium sulfite
With sulfuric acid at 150℃;
With sulfuric acid; sulfur trioxide at 140℃;

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + potassium sulfite + manganese dioxide → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2)

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + water (7732-18-5) + sodium sulfite → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2)

4-nitro-1-oxy-anthraquinone-sulfonic acid-(2) → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2)

Conditions	Yield
durch Reduktion und Ersatz der Amino-Gruppe durch die Hydroxyl-Gruppe;

1,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid sodium salt (22297-70-7) → 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2)

Conditions	Yield
With sulfuric acid; water pH=7;

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + [CoIII(tris(2-pyridylmethyl)amine)Cl2]Cl + sodium perchlorate → C50H41Co2N8O7S(3+)*3ClO4(1-)

Conditions	Yield
Stage #1: 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid; [CoIII(tris(2-pyridylmethyl)amine)Cl2]Cl With potassium hydroxide In water at 70℃; for 4h; Stage #2: sodium perchlorate In propan-1-ol; water at 4℃;	63%

ammonium hexafluorophosphate + [Co(tris(2-aminoethyl)amine)Cl2]Cl (20023-19-2) + 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → C26H41Co2N8O7S(3+)*3F6P(1-)

Conditions	Yield
Stage #1: [Co(tris(2-aminoethyl)amine)Cl2]Cl; 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid With potassium hydroxide In methanol at 60℃; Stage #2: ammonium hexafluorophosphate Reflux;	48%

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride bei gewoenlicher Temperatur und Behandlung des Reaktionsprodukts mit warmem Wasser;
With sodium dithionite; tin(ll) chloride bei gewoenlicher Temperatur und Behandlung des Reaktionsprodukts mit warmem Wasser;
With sodium dithionite; water at 95 - 100℃;
With sodium dithionite; water at 95 - 100℃;

morpholine (110-91-8) + formaldehyd (50-00-0) + 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → 1,4-dihydroxy-2-morpholin-4-ylmethyl-anthraquinone (56670-77-0)

Conditions	Yield
With sodium dithionite In ethanol; water

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → 1,4,9,10-Tetrahydroxy-anthracene-2-sulfonic acid

Conditions	Yield
In water at 25℃; Mechanism; effect of height of the mercury column, pH, concentration, temperature;

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + water (7732-18-5) → 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + natrium carbonate solution → 1,4-dihydroxy-9,10-anthracenedione (81-64-1)

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + aqueous Na2S2O4 → leucoquinizarine-sulfonic acid-(2)

hydrogenchloride (7647-01-0) + 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) + tin (II)-chloride → leucoquinizarine-sulfonic acid-(2)

hexaaquairon(III) (15377-81-8, 188867-80-3, 847043-81-6) + 1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → Fe(OH2)4(C14H6O7S)(1+) + Fe(OH2)4(C14H6O7S)(1+)

Conditions	Yield
With perchloric acid; sodium perchlorate In water Kinetics; 25°C, in O.5 M NaClO4/HClO4; stopped-flow kinetic studies;

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → C14H12O7S

Conditions	Yield
With hydrogenchloride; zinc In water at 47℃; for 3h; Temperature; Autoclave;

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → C16H18N2O5S

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; zinc / water / 3 h / 47 °C / Autoclave 2: ammonium hydroxide / 46 - 85 °C / Autoclave View Scheme

1,4-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (145-48-2) → 1-amino-4 (ethylamino)-9,10-anthraquinone-2-sulfonic acid (52373-92-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; zinc / water / 3 h / 47 °C / Autoclave 2: ammonium hydroxide / 46 - 85 °C / Autoclave 3: zinc(II) chloride / 63 °C View Scheme

Upstream product

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 7732-18-5 water 
• 22297-70-7 1,4-dihydroxy-9,10-dioxo-2-anthracenesulfonic acid sodium salt 

Downstream Products

• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 52373-92-9 1-amino-4 (ethylamino)-9,10-anthraquinone-2-sulfonic acid 

Relevant articles and documents

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.

ORGANIC ELECTROLYTE COMPOUNDS FOR REDOX-FLOW BATTERIES

The present invention relates to redox electrolyte compounds. The present invention further relates to a redox-flow battery wherein one of the catholyte and the anolyte, or both, has the redox electrolyte compound of the invention. The present invention further relates to the method of controlling the redox-flow battery and its use for energy storage.