641-13-4

Basic information

• Product Name: dibenzo[def,mno]chrysene-6,12-dione
• Synonyms: dibenzo[def,mno]chrysene-6,12-dione;anthanthrone;Anthranthrone;ANTHANTHRENEQUINONE;Einecs 211-372-0;Anthanthrone orange;Helanthrene Orange GK;NSC 30986
• CAS NO: 641-13-4
• Molecular Formula: C₂₂H₁₀O₂
• Molecular Weight: 306.3136
• EINECS: 211-372-0
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 641-13-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 415℃
• Boiling Point: 595.2°C at 760 mmHg
• Flash Point: 216.3°C
• Appearance: /
• Density: 1.507±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.9E-14mmHg at 25°C
• Refractive Index: 1.875
• CAS DataBase Reference: dibenzo[def,mno]chrysene-6,12-dione(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzo[def,mno]chrysene-6,12-dione(641-13-4)
• EPA Substance Registry System: dibenzo[def,mno]chrysene-6,12-dione(641-13-4)

Safety Data

• Hazardous Substances Data: 641-13-4(Hazardous Substances Data)

Usage

Purification Methods

Crystallise it from chlorobenzene, nitrobenzene or CHCl3 (m 340o). [Beilstein 7 I 451, 7 II 783, 7 III 4406, 7 IV 2694.]

InChI:InChI=1/C22H10O2/c23-21-13-5-1-3-11-7-9-16-19(17(11)13)20-15(21)10-8-12-4-2-6-14(18(12)20)22(16)24/h1-10H

Synthetic route

[1,1']binaphthyl-8,8'-dicarboxylic acid (10507-64-9, 10507-65-0, 29878-91-9) → anthanthrone (641-13-4)

Conditions	Yield
With sulfuric acid at 150 - 200℃; under 20 - 30 Torr;	91%
With sulfuric acid
With sulfuric acid at 60℃;

anthranthrene (191-26-4) + Mangantriacetat → anthanthrone (641-13-4) + 6,12-diacetoxyanthanthrene (141396-66-9) + 6-acetoxyanthanthrene (141396-65-8)

Conditions	Yield
In acetic acid; benzene at 40℃; for 5h;	A n/a B 19% C 47%
In acetic acid; benzene at 40℃; Rate constant;

anthranthrene (191-26-4) → anthanthrone (641-13-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

7-oxo-7H-dibenzo[a,kl]anthracene-13-carboxylic acid (10507-54-7, 10507-55-8, 60848-00-2) → anthanthrone (641-13-4)

Conditions	Yield
With potassium hydroxide at 180 - 230℃;

1,1'-binaphthyl-2,2'-dicarboxylic acid (18531-96-9, 80703-23-7, 99827-46-0) → anthanthrone (641-13-4)

Conditions	Yield
With sulfuric acid at 100℃;
With chlorosulfonic acid
With phosphorus pentachloride; nitrobenzene Versetzen des Reaktionsgemisches mit AlCl3;

[1,1']binaphthyl-8,8'-dicarboxylic acid acetic acid-anhydride → anthanthrone (641-13-4)

Conditions	Yield
at 200℃;
at 200℃;

acetic anhydride (108-24-7) + [1,1']binaphthyl-8,8'-dicarboxylic acid (10507-64-9, 10507-65-0, 29878-91-9) → anthanthrone (641-13-4) + 7-oxo-7H-dibenzo[a,kl]anthracene-13-carboxylic acid (10507-54-7, 10507-55-8, 60848-00-2)

Conditions	Yield
at 150 - 160℃;

C26H6O8 → anthanthrone (641-13-4)

Conditions	Yield
With copper diacetate; copper; acetic acid In quinoline Heating;

sulfuric acid (7664-93-9) + [1,1']binaphthyl-8,8'-dicarboxylic acid (10507-64-9, 10507-65-0, 29878-91-9) → anthanthrone (641-13-4)

Conditions	Yield
at 60℃;

<1.1'>binaphthyl-dicarboxylic acid-(8.8')-dimethyl ester → anthanthrone (641-13-4)

Conditions	Yield
With sulfuric acid

ammonium salt of/the/ 7-oxo-7H-dibenz<#a.kl!>anthracene-carboxylic acid-(13) → anthanthrone (641-13-4)

dinaphthyl-(1.1')-dicarboxylic acid-(2.2')-diethyl ester → anthanthrone (641-13-4)

Conditions	Yield
With sulfuric acid
With sulfuric acid

dinaphthyl-(1.1')-dicarboxylic acid-(8.8')-diethyl ester → anthanthrone (641-13-4)

Conditions	Yield
With sulfuric acid
With sulfuric acid

silver-salt of/the/ 7-oxo-7H-dibenz<#a.kl!>anthracene-carboxylic acid-(13) → anthanthrone (641-13-4)

methyl 8-bromonaphthoate (38058-95-6) + 5-bromo-2-iodo-benzoic acid methyl ester (181765-86-6) + copper-powder → anthanthrone (641-13-4) + 9-bromo-7-oxo-7H-benz[de]anthracene-11-carboxylic acid (860520-09-8)

Conditions	Yield
at 180℃; Erwaermen des Reaktionsprodukts mit Schwefelsaeure;

methyl 8-bromonaphthoate (38058-95-6) + methyl 2-bromo-5-nitrobenzoate (6942-36-5) + copper-powder → anthanthrone (641-13-4) + 9-nitro-7-oxo-7H-benz[de]anthracene-11-carboxylic acid

Conditions	Yield
at 180℃; Erwaermen des jeweiligen Reaktionsprodukts mit Schwefelsaeure;

methyl 8-bromonaphthoate (38058-95-6) + methyl 2-iodo-5-nitrobenzoate (112239-00-6) + copper-powder → anthanthrone (641-13-4) + 9-nitro-7-oxo-7H-benz[de]anthracene-11-carboxylic acid

Conditions	Yield
at 180℃; Erwaermen des jeweiligen Reaktionsprodukts mit Schwefelsaeure;

phosphorus pentachloride (10026-13-8, 874483-75-7) + 1,1'-binaphthyl-2,2'-dicarboxylic acid (18531-96-9, 80703-23-7, 99827-46-0) → anthanthrone (641-13-4)

Conditions	Yield
nachfolgend Einw. von Aluminiumchlorid in Nitrobenzol;

7-oxo-7H-dibenzo[a,kl]anthracene-13-carboxylic acid (10507-54-7, 10507-55-8, 60848-00-2) + potassium hydroxide → anthanthrone (641-13-4)

Conditions	Yield
at 230℃;

sulfuric acid (7664-93-9) + [1,1']binaphthyl-2,2'-dicarboxylic acid diethyl ester → anthanthrone (641-13-4)

sulfuric acid (7664-93-9) + [1,1']binaphthyl-8,8'-dicarboxylic acid diethyl ester (861599-70-4) → anthanthrone (641-13-4)

sulfuric acid (7664-93-9) + (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid (746-46-3, 18531-96-9, 80703-23-7, 99827-46-0) → anthanthrone (641-13-4)

Conditions	Yield
at 100℃;

anthranthrene (191-26-4) → anthanthrone (641-13-4) + anthanthrene 1,6-quinone + anthanthrene 3,6-quinone

Conditions	Yield
With sodium dichromate

anthanthrone (641-13-4) + lithium triisopropylsilyl acetylide → 6,12-bis(triisopropylsilylethynyl)dibenzo[def,mno]chrysene (1358795-33-1)

Conditions	Yield
Stage #1: lithium triisopropylsilyl acetylide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: anthanthrone With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; water at 0 - 20℃; for 3h;	82%

anthanthrone (641-13-4) → anthranthrene (191-26-4)

Conditions	Yield
With zinc	39%
With aluminium cyclohexylate; cyclohexanol

morpholine (110-91-8) + anthanthrone (641-13-4) → 3,9-dimorpholino-dibenzo[def,MnO]chrysene-6,12-dione

Conditions	Yield
With sodium amide

anthanthrone (641-13-4) → 4,10-dichloro-dibenzo[def,MnO]chrysene-6,12-dione (73944-28-2)

Conditions	Yield
With sulfuric acid; iodine; chlorine at 45 - 50℃;
With sulfuric acid; chlorine; iron(II) sulfate at 45 - 50℃;
With sulfuryl dichloride; iodine; nitrobenzene

anthanthrone (641-13-4) → 4,10-dibromoanthanthrone (4378-61-4)

Conditions	Yield
With sulfuric acid; bromine; iodine at 100℃;
With bromine; iodine; nitrobenzene at 160℃;
With sulfuric acid; bromine; iodine at 100℃;

anthanthrone (641-13-4) → 2,9-diiodoanthanthrone (52000-68-7)

Conditions	Yield
With sulfuric acid; iodine
With sulfuric acid; iodine at 120 - 180℃;
Multi-step reaction with 3 steps 1: nitric acid 2: sodium sulfide 3: Diazotization.Umsetzen mit Kaliumjodid-Loesung View Scheme
Multi-step reaction with 3 steps 2: sodium sulfide 3: Diazotization.Umsetzen mit Kaliumjodid-Loesung View Scheme

anthanthrone (641-13-4) → dibenzo[def,MnO]chrysene-6,12-diol (141396-67-0)

Conditions	Yield
With sodium hydroxide; palladium at 55℃; Hydrogenation;
With sodium hydroxide; nickel at 55℃; Hydrogenation;

anthanthrone (641-13-4) → 4-bromo-dibenzo[def,MnO]chrysene-6,12-dione (162785-72-0)

Conditions	Yield
With sulfuric acid; bromine; iodine at 60℃;
With sulfuric acid; bromine; iodine at 60℃;

anthanthrone (641-13-4) → 4-iodo-dibenzo[def,MnO]chrysene-6,12-dione

Conditions	Yield
With sulfuric acid; potassium iodide at 80℃;
With sulfuric acid; iodine at 120℃; man erhitzt anschliessend auf 120-130grad;

anthanthrone (641-13-4) → 4-chloro-dibenzo[def,MnO]chrysene-6,12-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: 90 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid 2: 90 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrogenchloride; sodium chlorate / 90 °C View Scheme

anthanthrone (641-13-4) → 3,9-dihydroxy-dibenzo[def,MnO]chrysene-6,12-dione (872294-43-4)

Conditions	Yield
With manganese(IV) oxide; potassium hydroxide

anthanthrone (641-13-4) → 4-bromo-10-chloro-dibenzo[def,MnO]chrysene-6,12-dione

Conditions	Yield
durch stufenweise Halogenierung;

anthanthrone (641-13-4) → 4-nitro-dibenzo[def,MnO]chrysene-6,12-dione

Conditions	Yield
With nitric acid; nitrobenzene
With nitric acid; nitrobenzene

anthanthrone (641-13-4) → 6,12-dioxo-6,12-dihydro-dibenzo[def,MnO]chrysene-4-sulfonic acid

Conditions	Yield
With sulfuric acid

anthanthrone (641-13-4) → 4,10-dinitro-dibenzo[def,MnO]chrysene-6,12-dione (96962-92-4)

Conditions	Yield
With sulfuric acid; potassium nitrate
With sulfuric acid; potassium nitrate
With nitric acid

anthanthrone (641-13-4) → 6,12-bis-sulfooxy-dibenzo[def,MnO]chrysene (114305-70-3)

Conditions	Yield
With pyridine; chlorosulfonic acid; iron

anthanthrone (641-13-4) + acetic anhydride (108-24-7) → 6,12-diacetoxyanthanthrene (141396-66-9)

Conditions	Yield
With zinc

2,4-Dinitrophenol (51-28-5) + anthanthrone (641-13-4) → C22H11O2

Conditions	Yield
In benzene at 20℃; Rate constant; Quantum yield; Irradiation; also in MeCN;

4-nitro-phenol (100-02-7) + anthanthrone (641-13-4) → C22H11O2

Conditions	Yield
In benzene at 20℃; Rate constant; Quantum yield; Irradiation; also in MeCN;

Mesitol (527-60-6) + anthanthrone (641-13-4) → C22H11O2

Conditions	Yield
In benzene at 20℃; Rate constant; Quantum yield; Irradiation; also in MeCN;

4-Phenylphenol (92-69-3) + anthanthrone (641-13-4) → C22H11O2

Conditions	Yield
In benzene at 20℃; Rate constant; Quantum yield; Irradiation; also in MeCN;

meta-nitrophenol (554-84-7) + anthanthrone (641-13-4) → C22H11O2

Conditions	Yield
In benzene at 20℃; Rate constant; Quantum yield; Irradiation; also in MeCN;

Upstream product

• 10026-13-8 phosphorus pentachloride 
• 18531-96-9 1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 10507-54-7 7-oxo-7H-dibenzo[a,kl]anthracene-13-carboxylic acid 
• 7664-93-9 sulfuric acid 
• 861599-70-4 [1,1']binaphthyl-8,8'-dicarboxylic acid diethyl ester 
• 191-26-4 anthranthrene 
• 746-46-3 (R)-1,1'-binaphthyl-2,2'-dicarboxylic acid 
• 38058-95-6 methyl 8-bromonaphthoate 
• 112239-00-6 methyl 2-iodo-5-nitrobenzoate 
• 6942-36-5 methyl 2-bromo-5-nitrobenzoate 
• 181765-86-6 5-bromo-2-iodo-benzoic acid methyl ester 
• 10507-64-9 [1,1']binaphthyl-8,8'-dicarboxylic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 191-26-4 anthranthrene 
• 4378-61-4 4,10-dibromoanthanthrone 

Relevant articles and documents

Production method of solid superacid catalyzed synthesis of anthracene ketone

The production method comprises the following steps: batching 1, 1 ˊ -binaphthalene -8, 8 ˊ -dicarboxylic acid into a proper amount of solvent, and then adding a solid superacid catalyst. The main reaction: temperature rise to reflux, dehydration. Until the reaction was complete, cooling down. After the product is purified, after the main reaction is finished, the solvent in the filter cake is filtered and removed, and then the filter cake is put into an aqueous sodium hydroxide solution for temperature rising, stirring and dissolution of incomplete 1, 1 ˊ -naphthalene -8, 8 ˊ - dicarboxylic acid and impurities and in the filter cake. The product is filtered and dried to obtain a product. To the invention, solid superacid is used as a catalyst, 1, 1 ˊ -binaphthalene -8 and 8 ˊ - dicarboxylic acid are subjected to catalytic dehydration condensation in an organic solvent to obtain the anthracene ketone with higher yield and purity. The pollution problem of waste sulfuric acid in the traditional process is solved.

Acid-Catalyzed Cyclization of o-Aroylbenzoic and Diarylcarboxylic Acids upon Heating in Vacuum

The cyclization of 1,1′-dinaphthyl-8,8′-dicarboxylic acid, diphenic anhydride, o-benzoylbenzoic acid, and 1-naphthoyl-o-benzoic acid into, respectively, anthanthrone, fluorenone-4-carboxylic acid, anthraquinone, and 1,2-benzanthraquinone occurs upon heating to 150-200°C in vacuum in the presence of catalytic amounts (1-3%) of H2SO4 or P2O5.