84-60-6

Basic information

• Product Name: 2,6-DIHYDROXYANTHRAQUINONE
• Synonyms: 10-Anthracenedione,2,6-dihydroxy-9;Anthrafravic acid;Anthraflavic acid,2,6-Dihydroxyanthraquinone, Anthraflavine;2,6-Dihydroxyanthraquinone, 94% 5GR;2,6-Dihydroxyanthracene-9,10-dione;2,6-Dihydroxy-9,10-anthracenedione;2,6-Dihydroxy-9,10-anthraquinone;Anthraflavic acid technical grade, 90%
• CAS NO: 84-60-6
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21
• EINECS: 201-544-3
• Product Categories: Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Highly Purified Reagents;Hydroxyanthraquinones;Other Categories;Refined Products by Sublimation
• Mol File: 84-60-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: >320 °C(lit.)
• Boiling Point: 342.92°C (rough estimate)
• Flash Point: 235.3 ºC
• Appearance: solid
• Density: 1.3032 (rough estimate)
• Vapor Pressure: 1.99E-08mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.72±0.20(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,6-DIHYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIHYDROXYANTHRAQUINONE(84-60-6)
• EPA Substance Registry System: 2,6-DIHYDROXYANTHRAQUINONE(84-60-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37
• WGK Germany: 3
• RTECS: CB6675000
• Hazardous Substances Data: 84-60-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

Uses

Anthraflavic acid can be used as a starting material to synthesize tetrahydroxy tetrathiafulvalene (TTF) derivatives, which are used as redox-active building blocks in supramolecular and materials science. It is also utilized to prepare phosphanylidene anthra[2,1-b]furans by reacting with dialkyl acetylenedicarboxylates and triphenylphosphine.

Definition

ChEBI: A dihydroxyanthraquinone that is anthracene substituted by hydroxy groups at C-3 and C-7 and oxo groups at C-9 and C-10.

InChI:InChI=1/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H

Synthetic route

Anthraquinone-2,6-disulfonic acid (84-50-4) → anthraflavic acid (84-60-6) + 2,3,6-trihydroxyacetophenone (85918-30-5)

Conditions	Yield
With potassium carbonate

Anthraquinone-2,6-disulfonic acid (84-50-4) → anthraflavic acid (84-60-6) + 1,2,6-trihydroxyanthraquinone (82-29-1)

Conditions	Yield
With sodium hydroxide; potassium nitrate

4-hydroxy-2-(4-methoxy-benzoyl)-benzoic acid (860597-60-0) → anthraflavic acid (84-60-6)

Conditions	Yield
With boron trioxide; sulfuric acid at 100℃; durch Erhitzen des Reaktionsprodukts mit AlCl3 auf 230grad;

3-Carboxyphenol (99-06-9) → 1,5-dihydroxyanthraquinone (117-12-4) + anthraflavic acid (84-60-6) + 1,7-dihydroxy-anthraquinone (569-08-4)

Conditions	Yield
at 350℃; Leiten des Dampfes unter vermindertem Druck durch ein mit Tonscherben gefuelltes Rohr;
at 330℃;

3-Carboxyphenol (99-06-9) → anthraflavic acid (84-60-6)

Conditions	Yield
trennt man vom 1.7-Dioxy-anthrachinon durch Umkrystallisieren aus Pyridin;

3-Carboxyphenol (99-06-9) → anthraflavic acid (84-60-6) + 1,7-dihydroxy-anthraquinone (569-08-4)

Conditions	Yield
With sulfuric acid at 180 - 200℃;

anthracene (120-12-7) → 2-Hydroxy-1,4-naphthoquinone (83-72-7) + 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + anthraflavic acid (84-60-6) + phenol (108-95-2)

Conditions	Yield
In water Oxidation; Formation of xenobiotics; simulated solar irradiation; Further byproducts given;

9,10-phenanthrenequinone (84-65-1) + alkaline solution + sodium sulfite + nitric → 1,2-dihydroxy-9,10-anthracenedione (72-48-0) + anthraflavic acid (84-60-6) + 1.2.6-trioxy-anthraquinone + 1.2.7-trioxy-anthraquinone

Conditions	Yield
at 180 - 200℃; unter Druck und Behandeln des Reaktionsproduktes mit Luft;

sulfuric acid (7664-93-9) + 3-Carboxyphenol (99-06-9) → 1,5-dihydroxyanthraquinone (117-12-4) + anthraflavic acid (84-60-6) + metabenzdioxyanthraquinone

Conditions	Yield
at 180 - 200℃; im geschlossenen Rohr;

sulfuric acid (7664-93-9) + water (7732-18-5) + 3-Carboxyphenol (99-06-9) + benzoic acid (65-85-0) → 1,5-dihydroxyanthraquinone (117-12-4) + anthraflavic acid (84-60-6) + metabenzdioxyanthraquinone

Conditions	Yield
at 180 - 200℃;

diazotized 2,6-diamino-anthraquinone → anthraflavic acid (84-60-6)

Conditions	Yield
With water

Anthraquinone-2,6-disulfonic acid (84-50-4) + extinguished lime/chalk/ → anthraflavic acid (84-60-6)

Conditions	Yield
Reaktion des Natriumsalzes;

sodium salt of/the/ 2-oxy-anthraquinone-sulfonic acid-(6) → anthraflavic acid (84-60-6)

Conditions	Yield
With alkaline earth; water at 170 - 180℃; unter Druck;

sodium salt of/the/ anthraquinone-disulfonic acid-(2.6>) → anthraflavic acid (84-60-6)

Conditions	Yield
With alkaline earth; water at 170 - 180℃; unter Druck;

3-Carboxyphenol (99-06-9) → anthraflavic acid (84-60-6) + 1.5-dihydroxy-anthraquinone and 1.7-dihydroxy-anthraquinone

Conditions	Yield
beim Leiten des mit Stickstoff verduennten Dampfes durch ein auf 330grad erhitztes Rohr;
beim Leiten des Dampfes unter vermindertem Druck durch ein mit Tonscherben gefuelltes, auf 350grad erhitztes Rohr;

3-Carboxyphenol (99-06-9) → anthraflavic acid (84-60-6) + anthrarufin, metabenzdioxyanthraquinone

Conditions	Yield
With sulfuric acid at 180 - 200℃;

6-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid (16067-07-5) + quicklime → anthraflavic acid (84-60-6)

Conditions	Yield
beim Verschmelzen;

hydrogenchloride (7647-01-0) + 2,6-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid → anthraflavic acid (84-60-6)

Conditions	Yield
at 210 - 250℃;

hydrogenchloride (7647-01-0) + sulfuric acid (7664-93-9) + 2,6-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid → anthraflavic acid (84-60-6) + 3-Carboxyphenol (99-06-9)

Conditions	Yield
at 250℃;

2-(4-methoxy-benzoyl)-4-nitro-benzoic acid (63712-32-3) → anthraflavic acid (84-60-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: iron (II)-hydroxide; aqueous ammonia 2: ueber die Diazonium-Verbindung 3: B2O3; fuming sulfuric acid / 100 °C / durch Erhitzen des Reaktionsprodukts mit AlCl3 auf 230grad View Scheme

4-amino-2-(4-methoxy-benzoyl)-benzoic acid (860561-54-2) → anthraflavic acid (84-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: ueber die Diazonium-Verbindung 2: B2O3; fuming sulfuric acid / 100 °C / durch Erhitzen des Reaktionsprodukts mit AlCl3 auf 230grad View Scheme

methoxybenzene (100-66-3) → anthraflavic acid (84-60-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: aluminium chloride 2: iron (II)-hydroxide; aqueous ammonia 3: ueber die Diazonium-Verbindung 4: B2O3; fuming sulfuric acid / 100 °C / durch Erhitzen des Reaktionsprodukts mit AlCl3 auf 230grad View Scheme

2,6-dihydroxyanthrone (60423-26-9) → anthraflavic acid (84-60-6) + di-(2,6-dihydroxy)anthrone

Conditions	Yield
With oxygen; potassium hydroxide In water for 120h;

anthraflavic acid (84-60-6) → 2,6-dihydroxyanthrone (60423-26-9)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water for 7h; Reflux;	97%
With ammonia; zinc
With hydrogenchloride; tin(ll) chloride Heating;

1 ,6-dibromohexane (629-03-8) + anthraflavic acid (84-60-6) → 2,6-bis(6-bromohexyloxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;	90%

1-bromo-hexane (111-25-1) + anthraflavic acid (84-60-6) → 2,6-bis(hexyloxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;	90%

1,4-dibromo-butane (110-52-1) + anthraflavic acid (84-60-6) → 2,6-bis(4-bromobutyloxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;	90%

anthraflavic acid (84-60-6) + 3,4,5-tris(tetradecyloxy)benzoic acid (179031-22-2) → 2,6-bis(3,4,5-tritetradecyloxybenzoyloxy)-9,10-anthraquinone (1079900-70-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h; Inert atmosphere;	89%

anthraflavic acid (84-60-6) + propyl bromide (106-94-5) → 2,6-dipropopxy-9,10-anthraquinone (1395499-87-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h;	88%

anthraflavic acid (84-60-6) + 1-iodo-2-{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}ethane (345915-45-9) → 2,6-bis{2-{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}ethoxy}anthraquinone (345915-47-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;	87%

anthraflavic acid (84-60-6) → anthracene-2,6-diol (101488-73-7)

Conditions	Yield
With sodium tetrahydroborate; sodium carbonate at 20℃; Inert atmosphere;	86%
With sodium tetrahydroborate; sodium carbonate at 20℃; for 29h; Inert atmosphere; Large scale;	80%
With ammonium hydroxide; aluminum amalgam In ethanol; water at 60 - 65℃; for 2h;	78%

anthraflavic acid (84-60-6) + methyl iodide (74-88-4) → 2,6-dimethoxy-9,10-anthracenedione (963-96-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	86%
With methanol; sodium hydroxide at 120℃;

anthraflavic acid (84-60-6) + 3,4,5-tridodecyloxy benzoic acid (117241-31-3) → 2,6-bis(3,4,5-tridodecyloxybenzoyloxy)-9,10-anthraquinone (1079900-68-7)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h; Inert atmosphere;	85%

anthraflavic acid (84-60-6) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) → dimethyl (E)-2-{2,6-dihydroxy-5-[3-methoxy-1-(methoxycarbonyl)-3-oxo-(1,1,1-triphenyl-λ5-phosphanylidene)propyl]-9,10-dioxo-9,10-dihydro-2-anthracenyl}-2-butenedioate (1240492-70-9)

Conditions	Yield
Stage #1: dimethyl acetylenedicarboxylate; triphenylphosphine at 20℃; for 0.4h; neat (no solvent); Stage #2: anthraflavic acid Grinding; neat (no solvent);	85%

bromocyane (506-68-3) + anthraflavic acid (84-60-6) → 2,6-dicyanatoanthraquinone (143814-17-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 10℃; for 0.5h;	84%

anthraflavic acid (84-60-6) + 4-(tetradecyloxy)benzoic acid (15872-46-5) → 2,6-bis(4-tetradecyloxybenzoyloxy)-9,10-anthraquinone (1079900-82-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h; Inert atmosphere;	84%

anthraflavic acid (84-60-6) + 4-(9H-carbazol-9-yl)benzoyl chloride → 2,6-bis[4-(carbazol-9-yl)benzoyloxy]anthraquinone

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide at 20℃; for 24h;	84%

anthraflavic acid (84-60-6) + 2-bromoethanol (540-51-2) → 2,6-bis(2-hydroxyethyloxy)-9,10-anthraquinone (500004-01-3)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80 - 90℃;	83%

4-octylbenzoic acid (3575-31-3) + anthraflavic acid (84-60-6) → C44H48O6

Conditions	Yield
Stage #1: anthraflavic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: 4-octylbenzoic acid In dichloromethane for 24h;	83%

anthraflavic acid (84-60-6) → C14H6Cl4O6P2 (129973-14-4)

Conditions	Yield
With phosphorus pentachloride In benzene for 1h; Heating;	80%

anthraflavic acid (84-60-6) + triphenylphosphine (603-35-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl (E)-2-{2,6-dihydroxy-5-[3-ethoxy-1-(ethoxycarbonyl)-3-oxo-(1,1,1-triphenyl-λ5-phosphanylidene)propyl]-9,10-dioxo-9,10-dihydro-2-anthracenyl}-2-butenedioate (1240492-71-0)

Conditions	Yield
Stage #1: triphenylphosphine; acetylenedicarboxylic acid diethyl ester at 20℃; for 0.4h; Grinding; neat (no solvent); Stage #2: anthraflavic acid neat (no solvent);	80%

anthraflavic acid (84-60-6) + acetic anhydride (108-24-7) → 2,6,9,10-tetraacetoxyanthracene (176391-92-7)

Conditions	Yield
With sodium acetate; zinc for 5h; Heating;	79%
With sodium acetate; zinc Behandeln des Produkts mit Alkohol und Umkrystallisieren des Rueckstands aus Eisessig;

anthraflavic acid (84-60-6) + dimethyl sulfate (77-78-1) → 2,6-dimethoxy-9,10-anthracenedione (963-96-2)

Conditions	Yield
With potassium carbonate In acetone for 8h; Reflux;	79%
With potassium carbonate In acetone at 100℃; for 5h; Inert atmosphere;	61%
With sodium carbonate at 150℃;

anthraflavic acid (84-60-6) + p-dodecyloxybenzoic acid (2312-15-4) → 2,6-bis(4-dodecyloxybenzoyloxy)-9,10-anthraquinone (1079900-78-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h; Inert atmosphere;	79%

anthraflavic acid (84-60-6) + 4-(diphenylamino)benzoyl chloride (25069-85-6) → 2,6-bis[4-(diphenylamino)benzoyloxy]anthraquinone

Conditions	Yield
With triethylamine In N,N-dimethyl acetamide at 20℃; for 24h;	79%

2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + anthraflavic acid (84-60-6) → 9,10-bis{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}anthracene

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 120℃; for 3h; Alkylation;	78%

anthraflavic acid (84-60-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 2,6-bis((tert-butyldimethylsilyl)oxy)anthracene-9,10-dione

Conditions	Yield
Stage #1: anthraflavic acid With sodium hydride In tetrahydrofuran for 1h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran for 12h;	78%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	78%

anthraflavic acid (84-60-6) + (2-bromoethoxy)(tert-butyl)diphenylsilane (139897-19-1) → 2,6-bis(2-tercbutyldiphenylsilyloxyethyloxy)-9,10-anthraquinone (345915-46-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h;	76%

2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + anthraflavic acid (84-60-6) → 2,6-bis{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}anthraquinone

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 120℃; for 2h;	76%

anthraflavic acid (84-60-6) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 9,10-bis-[(2,4-dinitro-phenyl)-hydrazono]-9,10-dihydro-anthracene-2,6-diol

Conditions	Yield
With sulfuric acid In methanol at 50℃; for 0.5h;	75%

anthraflavic acid (84-60-6) + 4-chloro-3-(trifluoromethyl)nitrobenzene (777-37-7) → 2,6-bis(2-trifluoromethyl-4-nitrophenoxy)anthraquinone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h;	74%

trifluoromethylsulfonic anhydride (358-23-6) + anthraflavic acid (84-60-6) → bistriflate of 2,6-dihydroxy-9,10-anthraquinone (131559-19-8)

Conditions	Yield
With pyridine at 20℃; for 12h;	73%
With pyridine at 20℃; for 15h; Inert atmosphere;	52%
With 2,6-dimethylpyridine; dmap In dichloromethane at 23℃;	36%

dilitium phthalocyanine + anthraflavic acid (84-60-6) → C14H8O4*C32H16N8(2-)*2Li(1+)

Conditions	Yield
In methanol for 72h; Reflux;	73%

Upstream product

• 99-06-9 3-Carboxyphenol 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 65-85-0 benzoic acid 
• 7647-01-0 hydrogenchloride 
• 60423-26-9 2,6-dihydroxyanthrone 
• 84-50-4 Anthraquinone-2,6-disulfonic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 120-12-7 anthracene 
• 860597-60-0 4-hydroxy-2-(4-methoxy-benzoyl)-benzoic acid 
• 63712-32-3 2-(4-methoxy-benzoyl)-4-nitro-benzoic acid 
• 100-66-3 methoxybenzene 
• 860561-54-2 4-amino-2-(4-methoxy-benzoyl)-benzoic acid 
• 16067-07-5 6-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 

Downstream Products

• 61169-36-6 1,2,4,5,6,8-hexahydroxy-9,10-anthraquinone 
• 101488-73-7 anthracene-2,6-diol 
• 33927-45-6 3-hydroxy-2,4,6-trinitro-benzoic acid 
• 17139-67-2 2,6-dihydroxy-1,5-dinitro-anthraquinone 
• 963-96-2 2,6-dimethoxy-9,10-anthracenedione 
• 159638-87-6 2,6-Bis<(tert-butyl-diphenylsilyl)oxy>anthraquinone 
• 85918-30-5 2,3,6-trihydroxyacetophenone 
• 120-12-7 anthracene 
• 13979-53-8 2,6-Diacetoxy-anthracen 
• 1747-94-0 2,6-Diacetoxy-anthrachinon 
• 345915-47-1 2,6-bis{2-{2-[(tert-butyldiphenylsilyl)oxy]ethoxy}ethoxy}anthraquinone 
• 345915-46-0 2,6-bis(2-tercbutyldiphenylsilyloxyethyloxy)-9,10-anthraquinone 

Relevant articles and documents

Extending the lifetime of organic flow batteries via redox state management

Redox flow batteries based on quinonebearing aqueous electrolytes have emerged as promising systems for energy storage from intermittent renewable sources. The lifetime of these batteries is limited by quinone stability. Here, we confirm that 2,6-dihydroxyanthrahydroquinone tends to form an anthrone intermediate that is vulnerable to subsequent irreversible dimerization. We demonstrate quantitatively that this decomposition pathway is responsible for the loss of battery capacity. Computational studies indicate that the driving force for anthrone formation is greater for anthraquinones with lower reduction potentials. We show that the decomposition can be substantially mitigated. We demonstrate that conditions minimizing anthrone formation and avoiding anthrone dimerization slow the capacity loss rate by over an order of magnitude. We anticipate that this mitigation strategy readily extends to other anthraquinone-based flow batteries and is thus an important step toward realizing renewable electricity storage through long-lived organic flow batteries.

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.