116-71-2

Usage

Uses

Used in Application Industry:
DIBENZANTHRONE is used as [application type] for [application reason]
Please provide the specific application industry and reason for the use of DIBENZANTHRONE.

Air & Water Reactions

Insoluble in water.

Fire Hazard

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

Flammability and Explosibility

Notclassified

TEST ITEMS

SPECIFICATION

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

VOLATITE 105 °C

1.0% max

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 
• 81-96-9 3-bromobenzanthrone 
• 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 
• 14205-06-2 [6,6']bi[benz[de]anthracenyl]-7,7'-dione 
• 1865-45-8 sodium anilide 
• 62-53-3 aniline 
• 188-87-4 violanthrene A 
• 7594-85-6 1-Benzoyl-4--naphthalin 
• 67-63-0 isopropyl alcohol 
• 7732-18-5 water 
• 108-95-2 phenol 

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 academic research and scientific papers

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.