84-65-1

Synthetic route

9,10-dihydroanthracene (613-31-0) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With oxygen In acetone at 20℃; under 760.051 Torr; for 10h; Reagent/catalyst; Solvent; Irradiation;	100%
With [bis(acetoxy)iodo]benzene; tert-butyl hydroxyperoxide; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol at 20℃; for 9h;	99%
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃;	99%

anthracene (120-12-7) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With nicotinium dichromate In acetic acid for 0.75h; Heating;	100%
With potassium bromate In acetic acid Heating;	100%
With ruthenium trichloride; dihydrogen peroxide; acetic acid	100%

anthracen-9(10H)-one (90-44-8) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With aluminum oxide; potassium permanganate; water In 1,2-dichloro-ethane for 75h; Ambient temperature;	100%
With aluminum oxide; potassium permanganate for 75h;	100%
With cerium(III) sulfate; barium bromate In water; acetonitrile for 20h; Heating;	97%

9,10-dihydro-9,10-dihydroxyanthracene (58343-58-1) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0333333h; Microwave irradiation;	100%
With tert.-butylhydroperoxide; RhCl(PPh3)3 In benzene at 70℃; for 48h;	87%
With tert.-butylhydroperoxide; RhCl(PPh3)3 In benzene at 70℃; for 48h;	87%

9-methylsulfinyl-10-(methylthio)anthracene → Dimethyldisulphide (624-92-0) + 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
Stage #1: 9-methylsulfinyl-10-(methylthio)anthracene With air; sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Rearrangement; Stage #2: With water; sodium hydrogencarbonate Hydrolysis;	A n/a B 100%

1-anthracen-9-yl-ethane-1,2-diol → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With osmium(VIII) oxide; trimethylamine-N-oxide In tetrahydrofuran; pyridine; water at 65℃;	100%

anthracene-9-boronic acid (100622-34-2) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst;	99.03%

9,10-dimethoxyanthracene (2395-97-3) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With zinc(II) nitrate; silica gel In tetrachloromethane for 0.25h; Heating;	98%
With hydrogenchloride; iodosylbenzene for 0.0833333h; Oxidation;	79%
With air; acetic acid Irradiation;
With bromine
With iodine

9-vinylanthracene (2444-68-0) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; for 72h;	98%

buta-1,3-diene (106-99-0) + hydroquinone (123-31-9) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With oxygen; pyrographite In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 120℃; under 760.051 Torr; for 48h; Schlenk technique; Cooling with ice;	98%

2-Benzoylbenzoic acid (85-52-9) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With sulfuric acid at 100℃;	97.8%
With sulfuric acid 1.) 140-200 deg C, vacuum 100-20 mm Hg, 2.) 180-200 deg C, 10 min;	93%
With Nafion-H In various solvent(s) at 180℃; for 3h; Acylation; Friedel-Crafts intramolecular acylation;	90%

9-anthracene aldehyde (642-31-9) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 4h; Reagent/catalyst; Solvent;	97%
With water; potassium bromide In chloroform at 25℃; for 1.56667h; pH=12; pH-value; Electrochemical reaction;	96%
With 1-ethyl-2,3-dimethylimidazolium iodide; sodium hydride In tetrahydrofuran at 20℃; for 72h;	46%
With potassium bromate In acetic acid for 0.5h; Heating;	80 mg
With tetrabutylammomium bromide; oxygen In dimethylsulfoxide-d6; chloroform-d1 at 25℃; for 8h; Reagent/catalyst; Irradiation;

N-(anthracen-9-yl)acetamide (37170-96-0) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With Selectfluor In methanol at 30℃; for 0.5h;	97%

9,10-dihydroanthracene (613-31-0) + [(C12H8N2)2Mn(μ-O)2Mn(C12H8N2)2](ClO4)4 → [(1,10-phenanthroline)2Mn(η1-OClO3)2] (100685-12-9, 463965-74-4) + anthracene (120-12-7) + anthracen-9(10H)-one (90-44-8) + 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
In acetonitrile Kinetics; the soln. in acetonitrile was allowed to stand overnight at room temp.; the organic products were detected by GC/MS; the soln. was layered with ether;	A n/a B 97% C 0.8% D 2%

9,10-bromoanthracene-9-carbaldehyde (93496-77-6) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 4h;	97%
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	95%

9,10-epidioxy-9,10-dihydroanthracene (4741-24-6) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 60℃;	74%

9-Bromoanthracene (1564-64-3) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	96%
With air; ethanol Irradiation.Sonnenlicht;
With osmium(VIII) oxide In hexane at 25℃; for 4.75h; Irradiation;
Multi-step reaction with 3 steps 1: potassium thioacetate; potassium phosphate; bis(dibenzylideneacetone)-palladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / toluene; acetone / 48 h / Inert atmosphere; Reflux 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Reflux 3: oxygen / 12 h / Irradiation View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C / Inert atmosphere 1.3: Inert atmosphere 2.1: oxygen / acetonitrile / 0.5 h / Irradiation View Scheme

9-Anthracenecarboxylic acid (723-62-6) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 3.5h;	96%
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	91%
With chromium(VI) oxide; acetic acid
With air
With perchloric acid; water In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere;

9,10-dihydroanthracene (613-31-0) → anthracene (120-12-7) + 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With tert.-butylhydroperoxide; H5PV2Mo10O40(1,11) In toluene for 24h; Ambient temperature;	A 96% B 4%
With dinitrogen monoxide; Ru(5,10,15,20-tetramesitylporphyrin)(O)2 In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Solvents; Reagents; Temperatures;	A 9% B 90%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In benzene at 200℃; under 7600 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;	A 9% B 90%

9-methoxyanthracene (2395-96-2) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	96%

10-benzhydrylidene-9-anthrone (667-91-4) → benzophenone (119-61-9) + 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction;	A 94% B 96%

1-<<(4-fluorophenyl)sulfonyl>oxy>-9,10-anthraquinone (123412-37-3) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With triethylammonium formate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In 1,4-dioxane at 90℃; for 0.5h; Product distribution;	95%

9-hydroxymethylanthracene (1468-95-7) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With sodium bromate; nitric acid; Nafion-Ce(IV) In acetonitrile for 1h; Heating;	95%
With sodium bromate; Nafion-Ce(IV); Nafion-H In water; acetonitrile for 4h; Heating;	90%
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	84%
With air In water-d2

anthracene; phenanthrene; mixture of → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
Stage #1: anthracene; phenanthrene; mixture of With manganese(II)carbonate; oxygen; acetic anhydride; acetic acid; sodium bromide at 100℃; for 24h; Stage #2: With water; dihydrogen peroxide at 50℃; for 2h;	95%

9,10-Diaminoanthrazene (53760-37-5) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With sodium periodate In water; ethyl acetate at 20℃; for 0.166667h;	95%
With [bis(acetoxy)iodo]benzene In acetone at 20℃; for 0.25h;	90%

1,4-dihydro-9,10-anthraquinone (885-19-8) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
palladium on activated charcoal In toluene for 12h; Heating;	94%
With air

9-methoxyanthracene-10-carboxaldehyde (63934-06-5) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;	94%
With N-Bromosuccinimide In water; N,N-dimethyl-formamide at 20 - 80℃; for 3h;	92%
bei der Oxydation;
With (bipyH2)-CrOCl5 In dichloromethane for 12h; Ambient temperature; other reagents, variation of conditions protic or aprotic media;

9,10-diacetoxy-9,10-dihydro-9,10-epidioxidoanthracene → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With sodium hydroxide In water; acetonitrile at 20℃; for 5h;	94%

9,10-dihydroanthracen-9,10-dicarbaldehyde (71440-45-4) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With tetrafluoroboric acid diethyl ether; iodosylbenzene In diethyl ether; dichloromethane at 20℃; for 2h;	93%

9,10-bis(trimethylsilyloxy)anthracene (28871-52-5) → 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With lithium perchlorate In acetonitrile anode potential 1.0 V vs. SCE, graphite felt anode, 2.5 F mol-1;	92%

9,10-phenanthrenequinone (84-65-1) → 9,10-Dihydroxyanthracene (4981-66-2)

Conditions	Yield
at 24.84℃; Kinetics; Quantum yield; UV-irradiation;	100%
With aluminium(III) iodide In acetonitrile for 1h; Heating;	70%
With sodiumsulfide nonahydrate In ethanol at 78℃; for 2h; Inert atmosphere;	10%

9,10-phenanthrenequinone (84-65-1) → 5,6-dihydro-6,11-dioxomorphanthridine (1143-50-6)

Conditions	Yield
With sodium azide; sulfuric acid In dichloromethane at 0 - 20℃;	100%
With sodium azide; sulfuric acid In chloroform at 20 - 40℃; for 4h;	97%
Stage #1: 9,10-phenanthrenequinone With sulfuric acid In dichloromethane at 0℃; Schlenk technique; Inert atmosphere; Stage #2: With sodium azide In dichloromethane at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere;	96%

9,10-phenanthrenequinone (84-65-1) + dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester (138519-02-5) → bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene (159638-86-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h;	100%
With n-butyllithium In tetrahydrofuran; hexane 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 1 h; -78 deg C to r.t., overnight;	38%

9,10-phenanthrenequinone (84-65-1) + allylindium sesquiiodide → 10-[1-(prop-2-enyl)]-10-hydroxy-9(10H)-anthracenone (32501-68-1)

Conditions	Yield
In N,N-dimethyl-formamide at -23℃; for 3h;	100%

N-benzylglycine (17136-36-6) + 9,10-phenanthrenequinone (84-65-1) → N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one

Conditions	Yield
With formaldehyd In 1,4-dioxane; benzene for 3h; Reflux; Dean-Stark;	100%

formaldehyd (50-00-0) + N-benzylglycine (17136-36-6) + 9,10-phenanthrenequinone (84-65-1) → N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one

Conditions	Yield
In 1,4-dioxane; benzene for 3h; Dean-Stark; Reflux;	100%

sodium metaborate + 9,10-phenanthrenequinone (84-65-1) → sodium perborate hexahydrate

Conditions	Yield
With oxygen; nickel In xylene in a cyclic oxidation process, anthraquinone in xylol/2-octanol (1:1) is reduced over Ni/H2, the cat. is removed and sodium metaborate (containing seed crystals of peroxoborate) is added; subsequent oxidation with O2 at 30°C for 20-30 min.;; containing 10% of active oxygene;;	99.5%
With O2; nickel In xylene; further solvent(s) in a cyclic oxidation process, anthraquinone in xylol/2-octanol (1:1) is reduced over Ni/H2, the cat. is removed and sodium metaborate (containing seed crystals of peroxoborate) is added; subsequent oxidation with O2 at 30°C for 20-30 min.;; containing 10% of active oxygene;;	99.5%

9,10-phenanthrenequinone (84-65-1) → 1-nitroanthraquinone (82-34-8)

Conditions	Yield
In water; nitric acid	99.2%
With phosphoric acid; sulfuric acid; nitric acid In tetrachloromethane for 6h; Ambient temperature;	90%
With nitric acid In water	71%

9,10-phenanthrenequinone (84-65-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 9,10-bis(formamido)anthracene (10303-96-5)

Conditions	Yield
for 12h; Reflux;	99%

9,10-phenanthrenequinone (84-65-1) → 9,10-dihydroanthracene (613-31-0)

Conditions	Yield
With hydrogen iodide; acetic acid for 120h; Heating;	99%
With phenylphosphane at 140℃; for 72h;	91%
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 8h;	91%

Conditions	Yield
With triphenylphosphine In benzene at 20℃; for 24h; Corey-Fuchs olefination;	99%
With triphenylphosphine In benzene at 20℃; for 24h;	96%
With triphenylphosphine In dichloromethane at 20℃;	91%

9,10-phenanthrenequinone (84-65-1) + glycerol (56-81-5) → 7H-benz[d,e]anthracene-7-one (82-05-3)

Conditions	Yield
Stage #1: 9,10-phenanthrenequinone With sulfuric acid; hydrogen; sodium dodecyl-sulfate In chlorobenzene under 10501.1 Torr; Heating; Stage #2: glycerol With sulfuric acid In chlorobenzene Reagent/catalyst; Pressure; Heating;	98.8%
in schwefelsaurer Loesung;
With sulfuric acid; acetic anhydride

9,10-phenanthrenequinone (84-65-1) → 1-anthraquinonesulfonic acid (82-49-5)

Conditions	Yield
In nitric acid-treated palladium; sulfuric acid	98%
With sulfuric acid; sulfur trioxide; mercury at 130℃;
With mercurosulfate; sulfuric acid; sulfur trioxide at 150℃;

maleonitrile (928-53-0, 764-42-1, 17656-09-6, 62600-65-1, 62742-11-4) + 9,10-phenanthrenequinone (84-65-1) → cis-11,12-Dicyano-9,10-ethano-9,10-dihydro-9,10-dihydroxyanthracene (132206-01-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In pyridine for 2h;	98%

9,10-phenanthrenequinone (84-65-1) + dimethyl 1,3-benzodithiol-2-ylphosphonate (62217-35-0) → 9,10-bis-(1,3-benzdithiol-2-ylidene)-9,10-dihydroanthracene (69213-08-7)

Conditions	Yield
Stage #1: dimethyl 1,3-benzodithiol-2-ylphosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Wittig-Horner reaction; Stage #2: 9,10-phenanthrenequinone In tetrahydrofuran; hexane at 20℃;	98%
With n-butyllithium 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 1 h -> r.t., 24 h; Yield given. Multistep reaction;

9,10-phenanthrenequinone (84-65-1) + aniline (62-53-3) → N,N'-diphenylanthroquinonediimine (34863-09-7)

Conditions	Yield
With aluminum (III) chloride; triethylamine In chloroform at 20℃; for 2h;	97.2%
With boric acid; tin(ll) chloride
With aluminium trichloride
With aluminum tri-bromide

9,10-phenanthrenequinone (84-65-1) + phenyltellurotrimethylsilane (73296-31-8) → 9,10-bis(trimethylsilyloxy)anthracene (28871-52-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; reductive silylation;	97%

Upstream product

• 71-23-8 propan-1-ol 
• 56-23-5 tetrachloromethane 
• 17407-25-9 10-benzylidene-9,10-dihydro-[9]anthrol 
• 79-21-0 peracetic acid 
• 120-12-7 anthracene 
• 85-52-9 2-Benzoylbenzoic acid 
• 85-44-9 phthalic anhydride 
• 71-43-2 benzene 
• 606-28-0 methyl o-benzoylbenzoate 
• 60-29-7 diethyl ether 
• 1560-32-3 10-bromo-10H-anthracen-9-one 
• 1705-94-8 acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester 
• 75-16-1 methylmagnesium bromide 
• 64-17-5 ethanol 

Downstream Products

• 50971-40-9 2-phenyl-quinoline-6-carboxylic acid 
• 78787-97-0 10-hydroxy-10-benzyl-9(10H)-anthracenone 
• 6321-62-6 9,10-Diaethyl-9,10-dihydro-anthracen-9,10-diol 
• 6318-17-8 anthranol 
• 860587-46-8 9,10-bis-(4-chloro-phenyl)-9,10-dihydro-anthracene-9,10-diol 
• 90-44-8 anthracen-9(10H)-one 
• 4981-66-2 9,10-Dihydroxyanthracene 
• 75-07-0 acetaldehyde 
• 17213-92-2 10-hydroxy-10-(4-hydroxy-4,4-diphenyl-but-1-ynyl)-anthrone 
• 873377-70-9 9,10-di-[2]naphthyl-9,10-dihydro-anthracene-9,10-diol 
• 113096-95-0 9,10-di(4-methylphenyl)-9,10-dihydroanthracene-9,10-diol 
• 120-12-7 anthracene 
• 873412-88-5 9,10-bis-biphenyl-4-yl-9,10-dihydro-anthracene-9,10-diol 
• 17213-89-7 10-hydroxy-10-(phenylethynyl)anthracen-9(10H)-one 

Relevant academic research and scientific papers

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Anthraquinone- and tetrahydroanthraquinone-catalysed pulping of Pinus radiata has given 10-methyl-9-anthrone (2) and derivatives (3) and (4), introduction of the carbon substituent involving carbohydrate constituents of the wood.

Anthrone complexation with aliphatic amines in an aprotic medium

Aromatic ketone (anthrone) complexation with aliphatic amines is studied by UV-Vis, 1H, 1H-1H COSY NMR spectroscopy. It is found that the catalytic activity of aliphatic amine is observed in the reaction of anthrone oxidation by molecular oxygen in aprotic media due to the formation of intermolecular complexes consisting of two anthrone molecules and one aliphatic amine molecule.

Novel highly stable β-cyclodextrin fullerene mixed valent Fe-metal framework for quick Fenton degradation of alizarin

β-Cyclodextrin (β-CD) supported magnetic nanoscaled fullerene/Fe3O4 (CDFMNPs) and fullerene/Fe3O4 (FMNPs) composites were prepared and characterized. These composites can be utilized as heterogeneous catalysts for the Fenton oxidation reaction to degrade alizarin in aqueous solutions. The saturation magnetization (Ms) value of quasi-spherical CDFMNPs was found to be 13.16 emu g-1 and their diameter was in the range of 25-30 nm. The catalytic activities of the prepared materials were tested with varying conditions of pH, amount used and the concentration of H2O2 for degradation of alizarin at room temperature. The exceptionally high degradation efficiency of CDFMNPs was observed for alizarin at pH 3 with 2.0 g L-1 catalyst and 25 mM of H2O2. The increased oxidative degradation efficiency is attributed mainly to the formation of active hydroxyl radicals (OH) on the surface of the catalyst, which are generated by the active decomposition of H2O2 by the solid heterogeneous catalyst and the promoting effect of β-CD. CDFMNPs can be magnetically separated and the catalyst was found to be reusable and stable for five successive runs with no significant loss of catalytic activity. In the magnetic environment of Fe3O4 nanoparticles, fullerene has a crucial role to enhance the activity by increasing the stability with nominal iron leaching. Based on mass analysis of alizarin degradation, the formation of aliphatic acids and monocyclic compounds through phthalic anhydride and di-methyl phthalate established the proposed degradation path.