116-71-2

Basic information

• Product Name: DIBENZANTHRONE
• Synonyms: sandothrenedarkbluenbo;sandothrenedarkbluenboa;sandothrenedarkbluenmba;Solanthrene Dark Blue B;Solanthrene Dark Blue BA;Solanthrene Dark Blue F-BA;solanthrenedarkblueb;solanthrenedarkblueba
• CAS NO: 116-71-2
• Molecular Formula: C₃₄H₁₆O₂
• Molecular Weight: 456.49
• EINECS: 204-152-0
• Product Categories: Organics
• Mol File: 116-71-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 338-339 °C
• Boiling Point: 522.64°C (rough estimate)
• Appearance: Bluish-black to black powder
• Density: 1.1055 (rough estimate)
• Refractive Index: 1.4875 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIBENZANTHRONE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZANTHRONE(116-71-2)
• EPA Substance Registry System: DIBENZANTHRONE(116-71-2)

Safety Data

• Hazardous Substances Data: 116-71-2(Hazardous Substances Data)

Usage

General Description

Bluish-black to black powder.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for DIBENZANTHRONE are not available. DIBENZANTHRONE is probably combustible.

Flammability and Explosibility

Notclassified

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE BLUE POWDER SHADE REDDISH HEAT RESISTANCE 300 °C min LIGHT FASTNESS 8 ACID RESISTANCE 5 ALKALI RESISTANCE 5 FASTNESS TO BLEEDING 5 OIL ABSORPTION 40-50% SPECIFIC SURFACE 27 m 2 /g DENSITY 1.60 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

BLUE POWDER

SHADE

REDDISH

HEAT RESISTANCE

300 °C min

LIGHT FASTNESS

8

ACID RESISTANCE

5

ALKALI RESISTANCE

5

FASTNESS TO BLEEDING

5

OIL ABSORPTION

40-50%

SPECIFIC SURFACE

27 m 2 /g

DENSITY

1.60 g/cm 3

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

InChI:InChI=1/C34H16O2/c35-33-25-7-3-1-5-17(25)19-9-11-21-22-12-10-20-18-6-2-4-8-26(18)34(36)28-16-14-24(30(22)32(20)28)23-13-15-27(33)31(19)29(21)23/h1-16H

Synthetic route

3-bromobenzanthrone (81-96-9) → 7H-benz[d,e]anthracene-7-one (82-05-3) + isoviolanthrone (116-71-2) + 13,13'-dibenzanthronyl (116-96-1)

Conditions	Yield
With potassium hydroxide; (Ph3P)2PdCl; hydrazine; alkyltrimethylammonium chloride In toluene at 90 - 95℃;	A n/a B 20% C n/a
Stage #1: 3-bromobenzanthrone With [2,2]bipyridinyl; nickel dichloride; zinc In N,N-dimethyl-formamide at 70℃; for 3h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 30 - 40℃; for 0.5h; Title compound not separated from byproducts;

7H-benz[d,e]anthracene-7-one (82-05-3) → isoviolanthrone (116-71-2)

Conditions	Yield
With methanol; potassium hydroxide; potassium acetate at 215℃; Reagens 4: Naphthalin; weitere Angaben: unter Zusatz von KClO3, NaNO2, MnO2 oder anderen Oxydationsmitteln;
With potassium hydroxide; ammonia; aluminium at 240℃;
With potassium hydroxide; formaldehyd; sodium acetate at 230 - 240℃;

7H-benz[d,e]anthracene-7-one (82-05-3) → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
With methanol; potassium hydroxide
With methanol; potassium hydroxide at 170 - 180℃; Behandeln des Reaktionsprodukts mit Luft;
With potassium hydroxide; ethanol at 170 - 180℃; Behandeln des Reaktionsprodukts mit Luft;

3-bromobenzanthrone (81-96-9) → isoviolanthrone (116-71-2)

Conditions	Yield
With potassium hydroxide; palladium on activated charcoal; Lindlar's catalyst; hydrazine hydrate at 139℃; under 7355.08 Torr;

4,4'-dibenzanthronyl (116-90-5) → isoviolanthrone (116-71-2)

Conditions	Yield
With aluminium trichloride; sodium chloride at 120 - 140℃; unter Zusatz von NaNO3, NaNO2 oder As2O5;
With potassium hydroxide beim Schmelzen; Behandeln des Reaktionsprodukts mit Luft;
With potassium hydroxide; sodium acetate at 230 - 240℃; Behandeln des Reaktionsprodukts mit Luft;

4,4'-dibenzanthronyl (116-90-5) → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
With potassium hydroxide at 190℃; nachfolgend Behandeln mit Luft;

13,13'-dibenzanthronyl (116-96-1) → isoviolanthrone (116-71-2)

Conditions	Yield
With potassium hydroxide; chlorobenzene at 80 - 120℃; Reagens 4: Methanol;
With potassium hydroxide; kerosine at 80 - 120℃; Reagens 4: Aethanol;
With potassium hydroxide; xylene at 80 - 120℃; Reagens 4: Methanol;

4.4'-Dibenzoyl-dinaphthyl-(1.1') (6404-64-4) → isoviolanthrone (116-71-2)

Conditions	Yield
With aluminium trichloride at 95 - 100℃;
With aluminium trichloride at 95 - 100℃;

7H-benzofluoren-7-one-6-carboxylic acid (52905-36-9) → isoviolanthrone (116-71-2)

Conditions	Yield
With potassium hydroxide at 300 - 360℃;

[6,6']bi[benz[de]anthracenyl]-7,7'-dione (14205-06-2) → isoviolanthrone (116-71-2)

Conditions	Yield
With potassium hydroxide; water at 260 - 270℃;

4,4'-dibenzanthronyl (116-90-5) + sodium anilide (1865-45-8) + aniline (62-53-3) → isoviolanthrone (116-71-2)

violanthrene A (188-87-4) → isoviolanthrone (116-71-2)

Conditions	Yield
With potassium dichromate; sulfuric acid

1-Benzoyl-4--naphthalin (7594-85-6) → isoviolanthrone (116-71-2)

Conditions	Yield
With aluminium trichloride

7H-benz[d,e]anthracene-7-one (82-05-3) + isopropyl alcohol (67-63-0) + potassium hydroxide → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
at 120 - 125℃; Product distribution; nachfolgend Einleiten von Luft;
at 120 - 125℃; Product distribution; nachfolgend Einleiten von Luft;

7H-benz[d,e]anthracene-7-one (82-05-3) + water (7732-18-5) + potassium hydroxide + potassium chlorate → isoviolanthrone (116-71-2) + 2-oxy-benzanthrone

Conditions	Yield
at 230 - 240℃; im Autoklaven;

7H-benz[d,e]anthracene-7-one (82-05-3) + phenol (108-95-2) + KOH → isoviolanthrone (116-71-2) + violanthrene-B

Conditions	Yield
at 220℃;

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

aluminium trichloride (7446-70-0) + 3,10-Dibromoperylene (85514-20-1) + benzoyl chloride (98-88-4) → isoviolanthrone (116-71-2)

Conditions	Yield
at 150 - 170℃;

4,4'-dibenzanthronyl (116-90-5) + sulfuric acid (7664-93-9) + mercury(II) sulfate → isoviolanthrone (116-71-2)

Conditions	Yield
at 200 - 240℃;
at 200 - 240℃;

aluminium trichloride (7446-70-0) + 4,4'-dibenzanthronyl (116-90-5) + 1,2,3-trichlorobenzene (87-61-6) → isoviolanthrone (116-71-2)

Conditions	Yield
at 140 - 150℃;

13,13'-dibenzanthronyl (116-96-1) + alcoholic KOH-solution → isoviolanthrone (116-71-2)

Conditions	Yield
at 115 - 130℃;
at 115 - 130℃;

13,13'-dibenzanthronyl (116-96-1) + sodium hydroxymethanesulfinate dihydrate (6035-47-8, 21135-92-2) + diluted NaOH-solution → isoviolanthrone (116-71-2)

Conditions	Yield
nachfolgend Behandeln mit Luft;
nachfolgend Behandeln mit Luft;

13,13'-dibenzanthronyl (116-96-1) + methanolic KOH-solution → isoviolanthrone (116-71-2)

Conditions	Yield
at 115 - 130℃;
at 115 - 130℃;

4,4'-dibenzanthronyl (116-90-5) + potassium hydroxide → isoviolanthrone (116-71-2)

4,4'-dibenzanthronyl (116-90-5) + sodium acetate (127-09-3) + potassium hydroxide → isoviolanthrone (116-71-2)

Conditions	Yield
at 230 - 240℃; Behandeln mit Luft;
at 230 - 240℃; Behandeln mit Luft;

4,4'-dibenzanthronyl (116-90-5) + methanolic KOH-solution → isoviolanthrone (116-71-2) + isoviolanthrone (128-64-3)

Conditions	Yield
at 170 - 180℃; nachfolgend Behandeln mit Luft;

7H-benz[d,e]anthracene-7-one (82-05-3) → isoviolanthrone (116-71-2) + 4-hydroxy-7-oxo-7H-benzanthracene, 'violanthrone-B'

Conditions	Yield
With potassium hydroxide; phenol at 220℃;

aluminium trichloride (7446-70-0) + 4.4'-Dibenzoyl-dinaphthyl-(1.1') (6404-64-4) → isoviolanthrone (116-71-2)

Conditions	Yield
at 95 - 100℃;
at 95 - 100℃;

quinoline (91-22-5) + 5,10-dioxo-5,10-dihydro-anthra[9,1,2-cde]benzo[rst]pentaphene-1,14-dicarboxylic acid + copper-powder → isoviolanthrone (116-71-2)

oxalyl dichloride (79-37-8) + isoviolanthrone (116-71-2) → dibenzo[a,def]pyranthrene-5,10,16,17-tetraone

Conditions	Yield
With aluminium trichloride; sodium chloride at 120 - 150℃;

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;

isoviolanthrone (116-71-2) → 5,10-dimethoxy-anthra[9,1,2-cde]benzo[rst]pentaphene (35081-34-6)

Conditions	Yield
With sodium carbonate; methyl p-toluene sulfonate; zinc weiteres Reagens: Trichlorbenzol;

isoviolanthrone (116-71-2) → violanthrene (81-31-2)

Conditions	Yield
With phosphorus; hydrogen iodide at 190℃;

isoviolanthrone (116-71-2) → 16-nitro-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione (128-60-9)

Conditions	Yield
With nitric acid; nitrobenzene at 25 - 28℃;

isoviolanthrone (116-71-2) → 5,10-dioxo-5,10-dihydro-anthra[9,1,2-cde]benzo[rst]pentaphene-3,12-disulfonic acid

Conditions	Yield
With sulfuric acid at 80℃;

isoviolanthrone (116-71-2) → 16-hydroxy-anthra[9,1,2-cde]pentaphene-5,10,17,18-tetraone

Conditions	Yield
With ammonium vanadate; nitrosylsulfuric acid at 120℃;

isoviolanthrone (116-71-2) → violanthrone-16,17-quinone (64346-54-9)

Conditions	Yield
With sulfuric acid; nitric acid
With manganese(IV) oxide; sulfuric acid; boric acid
With manganese(IV) oxide; sulfuric acid; boric acid
With sulfuric acid; nitric acid

isoviolanthrone (116-71-2) → 3,12-dibromo-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione (76415-41-3)

Conditions	Yield
With chlorosulphuric acid; sulfuric acid; bromine; iodine at 0 - 5℃;

isoviolanthrone (116-71-2) → 15,18-dichloro-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione (39170-98-4)

Conditions	Yield
With chlorine; 1,2-dichloro-benzene
With sulfuryl dichloride; nitrobenzene
With acetic acid at 100℃; beim Chlorieren;

isoviolanthrone (116-71-2) → 1,14-dibromo-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione (873973-42-3)

Conditions	Yield
With sulfuric acid; bromine; iodine at 100℃;

isoviolanthrone (116-71-2) → 15,16,17-trihydroxy-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione (72380-26-8)

Conditions	Yield
With nitrosylsulfuric acid; sulfuric acid at 110 - 115℃;
With nitrosylsulfuric acid; sulfuric acid; vanadia at 110 - 115℃;
With ammonium vanadate; sulfuric acid at 110 - 115℃;
With selenium(IV) oxide; sulfuric acid at 110 - 115℃;

isoviolanthrone (116-71-2) → 5,10-dioxo-16,17-sulfonyldioxy-5,10-dihydro-anthra[9,1,2-cde]benzo[rst]pentaphene-3,12-disulfonic acid

Conditions	Yield
With sulfuric acid; sulfur trioxide at 170℃;

isoviolanthrone (116-71-2) + acetic anhydride (108-24-7) → 16-acetyl-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione

Conditions	Yield
With aluminium trichloride; 1,2,3-trichlorobenzene at 140 - 180℃;

isoviolanthrone (116-71-2) + benzoyl chloride (98-88-4) → 16,17-dibenzoyl-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione

Conditions	Yield
With aluminium trichloride at 120 - 150℃;

isoviolanthrone (116-71-2) + methyl p-toluene sulfonate (80-48-8) → Jade Green XBN (128-58-5)

Conditions	Yield
With tetralin; sodium carbonate auf Siedetemperatur;
With potassium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;
With sodium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;

isoviolanthrone (116-71-2) + dimethyl sulfate (77-78-1) → Jade Green XBN (128-58-5)

Conditions	Yield
With potassium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;
With sodium carbonate; 1,2,3-trichlorobenzene unter Zusatz von Phenol, Naphthol-(1) oder Hydrochinon auf 180grad;

isoviolanthrone (116-71-2) → violanthrene A (188-87-4)

Conditions	Yield
With sodium chloride; zinc(II) chloride; zinc
With sodium chloride; zinc(II) chloride; zinc at 260℃;

Upstream product

• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 116-90-5 4,4'-dibenzanthronyl 
• 116-96-1 13,13'-dibenzanthronyl 
• 6404-64-4 4.4'-Dibenzoyl-dinaphthyl-(1.1') 
• 52905-36-9 7H-benzofluoren-7-one-6-carboxylic acid 
• 188-87-4 violanthrene A 
• 81-96-9 3-bromobenzanthrone 
• 7594-85-6 1-Benzoyl-4--naphthalin 
• 67-63-0 isopropyl alcohol 
• 7732-18-5 water 
• 108-95-2 phenol 
• 14205-06-2 [6,6']bi[benz[de]anthracenyl]-7,7'-dione 
• 1865-45-8 sodium anilide 
• 82-04-2 2-Chlorobenzanthrone 

Downstream Products

• 128-59-6 16,17-dihydroxyviolanthrene-5,10-dione 
• 81-31-2 Violanthren 
• 128-60-9 16-nitro-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione 
• 64346-54-9 violanthrone-16,17-quinone 
• 76415-41-3 3,12-dibromo-anthra[9,1,2-cde]benzo[rst]pentaphene-5,10-dione 
• 128-58-5 Jade Green XBN 
• 188-87-4 violanthrene A 
• 19339-29-8 Leucoviolanthren-dibenzoat 

Relevant articles and documents

Perylene derivatives formation in reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2 - 2,2′bipyridyl (or 1,10-phenathroline) - Zn

The reaction of 3-bromobenzanthrone and 4-bromonaphthalic acid derivatives with a reduction system NiCl2-2,2′bipyridyl (or 1,10-phenathroline)-Zn gives rise to compounds containing perylene fragment. Under similar conditions was established a possibility to transform substituted 1,1′-binaphthyls into the corresponding perylene derivatives.

CONVERSION OF 3-BROMOBENZANTHRONE INTO VIOLANTHRONE UNDER THE CONDITIONS OF CATALYSIS BY PALLADIUM COMPOUNDS

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