128-59-6

Basic information

• Product Name: DIHYDROXYDIBENZANTHRONE
• Synonyms: 16 17-DIHYDROXYDIBENZANTHRONE;16,17-DIHYDROXYVIOLANTHRONE;DIHYDROXYVIOLANTHRONE;DIHYDROXYDIBENZANTHRONE;16,17-dihydroxyviolanthrene-5,10-dione;16,17-Dihydroxybenzanthrone;16,17-Dihydroxydinaphtho [1,2,3-c,d,3',2',1'-l,m] perylene-5,10-dione;Anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione, 16,17-dihydroxy-
• CAS NO: 128-59-6
• Molecular Formula: C₃₄H₁₆O₄
• Molecular Weight: 488.49
• EINECS: 204-897-1
• Product Categories: Organics
• Mol File: 128-59-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 543.71°C (rough estimate)
• Appearance: /
• Density: 1.1524 (rough estimate)
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.10±0.20(Predicted)
• CAS DataBase Reference: DIHYDROXYDIBENZANTHRONE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROXYDIBENZANTHRONE(128-59-6)
• EPA Substance Registry System: DIHYDROXYDIBENZANTHRONE(128-59-6)

Safety Data

• Hazardous Substances Data: 128-59-6(Hazardous Substances Data)

Usage

General Description

Dihydroxydibenzanthrone is a chemical compound that belongs to the family of polycyclic aromatic compounds. It is a synthetic organic pigment that is commonly used as a blue colorant in various industrial applications, such as inks, coatings, and plastics. Dihydroxydibenzanthrone is known for its high color strength, excellent lightfastness, and weather resistance, making it suitable for outdoor and indoor applications. It is also widely used in the field of arts and crafts, where its vibrant and durable blue color makes it a popular choice for artists and manufacturers alike. Additionally, dihydroxydibenzanthrone has been found to have low acute toxicity, allowing it to be used safely in consumer products.

InChI:InChI=1/C34H16O4/c35-25-13-23-15-5-1-3-7-19(15)33(37)21-11-9-17-18-10-12-22-28-24(16-6-2-4-8-20(16)34(22)38)14-26(36)32(30(18)28)31(25)29(17)27(21)23/h1-14,35-36H

Synthetic route

7H-benz[d,e]anthracene-7-one (82-05-3) → 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid Verschmelzen des Reaktionsprodukts mit Alkalihydroxyd;

4,4'-dibenzanthronyl (116-90-5) → 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6)

Conditions	Yield
With manganese(IV) oxide; sulfuric acid

isoviolanthrone (116-71-2) → 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6)

Conditions	Yield
With sodium hydroxide; zinc anschlissenden Behandeln mit H2S;
With sodium hydroxide; zinc anschlissenden Behandeln mit Luft bei 90grad;
With sodium hydroxide; alkaline aqueous Na2S2O4 anschlissenden Behandeln mit Luft bei 90grad;

Jade Green XBN (128-58-5) → 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6)

Conditions	Yield
Stage #1: Jade Green XBN In dichloromethane at 20℃; for 1h; Stage #2: With boron tribromide In dichloromethane at 20℃; for 16h; Reflux; Cooling with ice;

1-bromo dodecane (112-29-8) + 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) → 16,17-didecyloxyviolanthrone

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; Williamson Ether Synthesis;	74%

1-bromo-octane (111-83-1) + 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) → 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (85652-50-2)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 8h; Williamson Ether Synthesis;	72%
Stage #1: 16,17-dihydroxyviolanthrene-5,10-dione With potassium carbonate In N,N-dimethyl-formamide at 120℃; Stage #2: 1-bromo-octane In N,N-dimethyl-formamide at 120 - 130℃; for 11h;	12.5%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + 1-dodecylbromide (143-15-7) → 16,17-didodecyloxyviolanthrone

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In dimethyl sulfoxide at 100℃; for 5h; Williamson Ether Synthesis;	69%

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + benzoyl chloride (98-88-4) → Leuco-16,17-dihydroxy-violanthron-tetrabenzoat (19339-25-4)

Conditions	Yield
With pyridine; zinc

1-bromo-hexane (111-25-1) + 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) → 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (25637-03-0)

Conditions	Yield
With potassium carbonate
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Williamson Ether Synthesis;

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + mercury(II) sulfate + nitrosylsulfuric acid → 15.16.17-trihydroxy-violanthrenedione-(5.10)

Conditions	Yield
at 150℃;

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 15.18-dinitro-16.17-dihydroxy-violanthrenedione-(5.10)(?)

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + nitric acid (7697-37-2) → isoviolanthrone (116-71-2)

pyridine (110-86-1) + 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + Stearoyl chloride (112-76-5) + zinc → 5,10,16,17-tetrakis-stearoyloxy-anthra[9,1,2-cde]benzo[rst]pentaphene

16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) + nitrobenzene (98-95-3) + dimethyl sulfate (77-78-1) + sodium carbonate → bz2.bz2'-dimethoxy-violanthrone

2-ethylhexyl bromide (18908-66-2) + 16,17-dihydroxyviolanthrene-5,10-dione (128-59-6) → 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (1027311-37-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;

Upstream product

• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 116-90-5 4,4'-dibenzanthronyl 
• 116-71-2 isoviolanthrone 
• 128-58-5 Jade Green XBN 

Downstream Products

• 19339-25-4 Leuco-16,17-dihydroxy-violanthron-tetrabenzoat 
• 116-71-2 isoviolanthrone 
• 85652-50-2 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione 
• 71550-33-9 16,17-didecyloxyviolanthrone 

Relevant articles and documents

Effect of substituents on the aggregate structure and photovoltaic property of violanthrone derivatives

In this paper, three violanthrone derivatives with different substituents, 16,17-bis(2-ethylhexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (3), 16,17-bis(octyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (4), 16,17-bis(hexyloxy)-anthra[9,1,2-cde-]benzo[rst]pentaphene-5,10-dione (5), are synthesized. It is found that the substituent has a great effect on the aggregate structures of violanthrone derivatives: the shorter the side chain is, the stronger the intermolecular π-π actions in the solid state is. Because all compounds are p-type semiconductive materials with the relatively low-lying highest occupied molecular orbital (HOMO) energy levels (～-5.1 eV) and low band gaps (～1.8 eV), their photovoltaic properties are evaluated when the blends of violanthrone derivatives and [6,6]-phenyl-C 61-butyric acid methyl ester (PCBM) (1:1, w/w) are used as the active layers of organic solar cells. Among three violanthrone derivatives, compound 5 exhibits the best photovoltaic performance with the power conversion efficiency (PCE) of 0.54% since the aggregate structure of compound 5 is in favor of charge transport.