84-65-1

Basic information

• Product Name: Anthraquinone
• Synonyms: Anthraquinone 97%;Anthraquinone Vetec(TM) reagent grade, 97%;MORKIT;9,10(9H,10H)-anthracenedione;9,10-Anthracenedione;9,10-anthracenequinone;9,10-Anthrachinon;9,10-dihydro-9,10-dioxo-anthracen
• CAS NO: 84-65-1
• Molecular Formula: C₁₄H₈O₂
• Molecular Weight: 208.21
• EINECS: 201-549-0
• Product Categories: Intermediates of Dyes and Pigments;Chloroanthraquine, etc.;Anthraquinones;AM to AQCarbonyl Compounds;A;Alphabetic;C13 to C14;Carbonyl Compounds;Ketones;AM to AQPesticides&Metabolites;A-BAlphabetic;Alpha sort;Others;Pesticides;Pesticides&Metabolites
• Mol File: 84-65-1.mol
• Article Data: 470

Chemical Properties

• Melting Point: 284-286 °C(lit.)
• Boiling Point: 379-381 °C(lit.)
• Flash Point: 365 °F
• Appearance: Yellow-green to khaki to tan/Powder
• Density: 1.438
• Vapor Density: 7.16 (vs air)
• Vapor Pressure: 1 mm Hg ( 190 °C)
• Refractive Index: 1.5681 (estimate)
• Storage Temp.: Storage temperature: no restrictions.
• Solubility: 0.00007g/l
• Water Solubility: <0.1 g/100 mL at 23℃
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• Merck: 14,687
• BRN: 390030
• CAS DataBase Reference: Anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: Anthraquinone(84-65-1)
• EPA Substance Registry System: Anthraquinone(84-65-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37/38
• Safety Statements: 36/37-37/39-26-24
• RIDADR: 3077
• WGK Germany: 1
• RTECS: CB4725000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 84-65-1(Hazardous Substances Data)

Usage

Chemical Properties

Anthraquinone is a combustible, light yellow to green crystalline solid. Soluble in ethanol, ether and acetone, insoluble in water. It may be prepared by reacting benzene with phthalic anhydride. The compoundis the basis of a range ofdyestuffs.

Occurrence

Anthraquinones naturally occur in some plants (eg. aloe, senna, rhubarb, and Cascara buckthorn), fungi, lichens, and insects, where they serve as a basic skeleton for their pigments. Natural anthraquinone derivatives tend to have laxative effects.

Uses

Anthraquinone is used in paper industry as a catalyst to increase the pulp production yield and to improves the fiber strength through reduction reaction of cellulose to carboxylic acid. It is also used as a precursor for dye formation.

Preparation

Anthraquinone is obtained by oxidation of anthracene using sodium dichromate plus sulfuric acid, and is purified by dissolving in concentrated sulfuric acid at 130 °C and pouring into boiling water, whereupon anthraquinone separates as pure solid, and is recovered by filtration. Further purification may be accomplished by sublimation or crystallization from nitrobenzene, aniline or tetrachloroethane.

Definition

ChEBI: Anthraquinone is an anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls. It is a colorless crystalline quinone used in producing dyestuffs such as alizarin.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 1457, 1980 DOI: 10.1021/ja00524a059The Journal of Organic Chemistry, 29, p. 987, 1964 DOI: 10.1021/jo01027a538Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

General Description

Anthraquinone is a polycyclic aromatic hydrocarbon derived from anthracene or phthalic anhydride. Anthraquinone is used in the manufacture of dyes, in the textile and pulp industries, and as a bird repellant.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Anthraquinone is incompatible with strong oxidizing agents.

Hazard

Possible carcinogen.

Fire Hazard

Anthraquinone is combustible.

Flammability and Explosibility

Nonflammable

Agricultural Uses

Repellent, Seed treatment: Used as a seed dressing or protectant. Banned in EU.

Trade name

(p)ANTHRAPEL?; FLIGHT CONTROL- PLUS?; HOELITE?; MORKIT?; REPELL?

Pharmacology

Anthraquinone is a secondary repellent and affects birds by causing post-ingestional distress (40). Sometimes, ingestion of anthraquinone-treated food produces vomiting, but often vomiting does not occur and the bird just sits quietly until the discomfort passes. Unlike methiocarb, anthraquinone doe not affect the bird’s nervous system and does not immobilize affected birds. Presumably, the emetic response is produced through irritation of the gut lining, but the actual mechanism is unclear. It is clear, however, that anthraquinone is not a taste repellent or contact irritant. Birds do not hesitate to eat treated food, and they exhibit no sign that treated food is unpalatable to them. The post-ingestional discomfort that results from eating anthraquinone-treated food produces a conditioned aversion to that food type. Birds need to experience the adverse consequences before learning to avoid the protected food. Thus, it is not reasonable to expect losses to cease immediately upon application of the repellent. There will be some level of loss in the crop as the depredating birds acquire the learned avoidance response.

Safety Profile

Moderately toxic by intraperitoneal route. A mild allergen. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, foam, CO2, water spray or mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Anthraquinone is an important starting material for vat dye manufacture. Also used in making organics; and used as a bird repellent in seeds.

Shipping

UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise anthraquinone from CHCl3 (38mL/g), *benzene, or boiling acetic acid, wash it with a little EtOH and dry it under vacuum over P2O5. [Beilstein 7 IV 2556.]

Toxicity evaluation

Anthraquinone is a stable compound that is virtually insoluble in water. It is not phytotoxic and does not inhibit germination of rice seeds or growth of sprouts. It has very low toxicity to birds and mammals, and it appears to be innocuous to insects as well. There is no known hazard to nontarget species from repellent applications of Flight Control.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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

• 85-52-9 2-Benzoylbenzoic acid 
• 1705-94-8 acetic acid 10-oxo-9,10-dihydro-anthracen-9-yl ester 
• 82-48-4 1,8-anthraquinonedisulphonic acid 
• 117-14-6 1,5-anthraquinone disulfonate 
• 82-49-5 1-anthraquinonesulfonic acid 
• 1560-32-3 10-bromo-10H-anthracen-9-one 
• 100-52-7 benzaldehyde 
• 93-89-0 benzoic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 124108-62-9 9-hydroxy-9H,9'H-[9,9']bianthryl-10,10'-dione 
• 71-43-2 benzene 
• 110-52-1 1,4-dibromo-butane 
• 90-44-8 anthracen-9(10H)-one 

Downstream Products

• 78787-97-0 10-hydroxy-10-benzyl-9(10H)-anthracenone 
• 4946-83-2 1-piperidinoanthraquinone 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 137124-55-1 9-hydroxy-9-(hydroxymethyl)anthrone 
• 68525-40-6 C₁₁H₁₅ 
• 434-85-5 9,9'-bianthrone dianion 
• 99838-41-2 9,10-dithioanthraquinone 
• 108709-23-5 2-(4-methoxyphenyl)-anthra<1,9-de>-1,3,2-oxathiaphosphorin-7-ol, 2-sulfide 
• 92-52-4 biphenyl 
• 602-55-1 9-phenylanthracene 
• 447-53-0 1,2-Dihydronaphthalene 
• 4981-66-2 9,10-Dihydroxyanthracene 
• 84-47-9 2-tert-butylanthraquinine 
• 101905-56-0 9,10-dihydroxy-9-t-butylanthracene 

Relevant articles and documents

Alcohol oxidation and aldol condensation during base-catalyzed reaction of primary alcohols with 1-chloroanthraquinone

When chloroanthraquinone is treated with primary alcohols under basic conditions, the notoriously low yields observed for substitution result in part from oxidation of the alcohol followed by aldol condensation. (C) 2000 Elsevier Science Ltd.

Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance of some 9,10-Anthraquinol Radicals in Solution

EPR, ENDOR and TRIPLE resonance spectra are recorded for 9,10-anthraquinol-1-sodium sulphonate, 9,10-anthraquinol-2-sodium sulphonate, 9,10-anthraquinol-1,5-disodium sulphonate and 9,10-anthraquinol-2,6-disodium sulphonate cation radicals.The splittings of the 9,10-anthraquinol cation radical have been assigned by deuteration.The spectra of the deuterated anthraquinol cation radicals and the assignment of hyperfine coupling constants are discussed.

Kinetics and mechanism of anthracene oxidation with tert-butyl hydroperoxide over metal-organic frameworks Cr-MIL-101 and Cr-MIL-100

The oxidation of anthracene (AN) with tert-butyl hydroperoxide (TBHP) over metal-organic frameworks (MOFs) Cr-MIL-101 and Cr-MIL-100 produced anthraquinone (AQ) in a nearly quantitative (>99%) yield after 1 and 4 h, respectively, at 100 °C in chlorobenzene (ClPh). At initial stages of the reaction, some amounts (a was found to be similar for MIL-101 and MIL-100 (15 kcal/mol) while pre-exponential factors were different (7·106 and 3·106 L/(mol·min), respectively). The kinetic results indicated that the AN oxidation with TBHP over both MIL-101 and MIL-100 is not controlled by diffusion. No adsorption of AN on the MOFs from ClPh solution was found at the reaction temperature. A mechanism that involves a reversible interaction between TBHP and CrIII centers within the MOF framework producing an active oxidizing species (rate-limiting step), followed by oxygen atom transfer from the peroxo species to the aromatic substrate to give primary oxygenated product(s), further oxidation of which leads to AQ, has been suggested.

Oxidation with the H2O2-VO3--pyrazine-2-carboxylic acid reagent 2. Oxidation of alcohols and aromatic hydrocarbons

Aromatic hydrocarbons are oxidized with hydrogen peroxide in the presence of catalytic amounts of VO3- and pyrazine-2-carboxylic acid into phenols (provided excess hydrocarbon is used) or into quinones (at high H2O2 concentrations). 2-Propanol, ethanol, cyclohexanol, and benzyl alcohol are transformed into the corresponding aldehydes and ketones under the same conditions (without a solvent or in MeCN). - Key words: oxidation, hydrogen peroxide, vanadium complexes; aromatic hydrocarbons; alcohols.

Pulse Radiolyses of Anthraquinone and Anthraquinone-Triethylamine in Acetonitrile and Toluene at Room Temperature

Nanosecond pulse radiolysis of anthraquinone (AQ) in several solvents has been performed at room temperature, and the following results are obtained: (1) In acetonitrile (CH3CN), the formation of triplet AQ and a free-radical anion (AQ.-) of AQ is observed.The former is produced by energy transfer from an excited neutral of CH3CN which may be produced via the geminate recombination of a radical cation and a radical anion of CH3CN in a spur, while the latter is produced by electron transfer from anionic species such as a solvated electron, a monomeric and/or dimeric radical anion of CH3CN.In CH3CN-triethylamine (TEA), both free AQ.- and triplet AQ mentioned above are also produced; however, the latter reacts with TEA, giving rise to the formation of free AQ.- (from the second triplet state of AQ) and an exciplex of the lowest triplet state of AQ with ground-state TEA.This exciplex decomposes to free AQ.- and the radical cation of TEA. (2) In toluene, only triplet AQ is produced by energy transfer from triplet toluene to AQ, and, in the presence of TEA, the formation of the triplet exciplex of AQ-TEA is observed.On a microsecond timescale, however, this exciplex changes to a contact ion pair followed by proton transfer, generating anthrasemiquinone radical and triethylamine radical in accordance with the result of photolysis.

Photoproducts of carminic acid formed by a composite from Manihot dulcis waste

Carbon-TiO2 composites were obtained from carbonised Manihot dulcis waste and TiO2 using glycerol as an additive and thermally treating the composites at 800 °C. Furthermore, carbon was obtained from manihot to study the adsorption,

INTRODUCTION OF ONE-CARBON UNITS DURING ANTHRAQUINONE-CATALYSED PULPING OF WOOD

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.

The influence of the structure of aliphatic amine on its catalytic activity in the oxidation of anthrone in dimethyl sulfoxide

The catalytic activity of several aliphatic amines in the liquid-phase oxidation of anthrone by molecular oxygen in dimethyl sulfoxide was studied. The kinetic data obtained were compared with the results of quantum-chemical calculations. The catalytic activity of aliphatic amines in the reaction under consideration was directly proportional to an increase in the absolute value of the heat of formation of the corresponding ammonium cation.

2,7-Dithia-, 2,8-Dithia-, and 2,9-Dithia(9,10)anthracenophanes. High Reactivity Induced by Aryl-Ring Deformation

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Matrix Isolation of 3,4-Benzocyclodeca-3,7,9-triene-1,5-diyne

3,4-Benzocyclodeca-3,7,9-triene-1,5-diyne (3) has been synthesized from two different precursors and characterized by means of matrix-isolation spectroscopy. Energies, structures and IR spectra of the product, the intermediate 9,10-didehydroanthracene (4), and of the transition state of the Bergman cyclization 3 → 4 have been calculated at the B3LYP/6-31G * level of theory.

Thermochromism at room temperature in overcrowded bistricyclic aromatic enes: Closely populated twisted and folded conformations

The overcrowded thermochromic bistricyclic aromatic enes (BAEs) 10-(9′H-fluoren-9′-ylidene)-9(10H)-anthracenone (6), 10-(11′H-benzo[b]fluoren-11′-ylidene)-9(10H)-anthracenone (7), and 10-(1′,8′-diaza-9′H-fluoren-9′-ylidene)-9(10H) -anthracenone (8) were synthesized by applying Barton's two-fold extrusion diazo-thione coupling method and their crystal and molecular structures were determined. BAEs 6-8 exhibit thermochromic behavior at room temperature due to the equilibrium between the yellow anti-folded conformations and the thermochromic purple, blue, or red twisted conformations. The NMR experiments demonstrate a fast interconversion of the twisted and the anti-folded conformers of 6-8 in solution. BAE 7 readily undergoes E,Z-topomerization at room temperature with the coalescence point at 297 K and the relatively low energy barrier of ΔGc?(t⊥) = 65.5 kJ/mol. B3LYP/6-311++G(d,p) calculations predict anti-folded a-6 and a-7 to be less stable than twisted t-6 and t-7 by 0.8 and 1.3 kJ/mol, respectively, whereas a-8 is more stable than t-8 by 10.7 kJ/mol. DFT calculations of 6-8, 9-(9′H-fluoren-9′-ylidene)-9H-fluorene (1), [10′-oxo- 9′(10′H)-anthracenylidene]-9(10H)-anthracenone (2) and their 1,8-diaza-substituted derivatives show that substitution in the fluorenylidene unit destabilizes the twisted conformations by 11-22 kJ/mol, while introduction of nitrogen atoms at the 1 and 8 positions of anthracenylidene unit destabilizes the anti-folded conformations by 14-18 kJ/mol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Quinaldinium Chlorochromate Supported on Alumina: A New and Efficient Reagent for the Oxidation of Alcohols

The new, mild chromium(VI) oxidizing agent, quinaldinium chlorochromate supported on neutral alumina, was prepared as a stable yellow solid. The reagent is suitable to oxidize various primary and secondary alcohols to the corresponding carbonyl compounds and anthracene to anthraquinone in good yields.

Kinetics of amine catalysed oxidation of anthrone by oxygen in aprotic solvents

Catalytic activity for the series of aliphatic and aromatic amines in liquid-phase oxidation of anthrone with molecular oxygen was studied gas-volumetrically and spectroscopically. It was shown that the studied amines are arranged in the following order of decreasing catalytic activity: NH 3 > RNH2 > R1R2NH > R 1R2R3N > ArNR2. A kinetic scheme for the process is proposed. Pleiades Publishing, Ltd., 2010.

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Anthracene-based fluorescence turn-on chemodosimeter for the recognition of persulfate anion

The anthracene thiosemicarbazone (ATSC) fluorescence 'turn-on' chemodosimeter for the detection of the persulfate anion (S2O82-) in 90% DMSO has been developed. ATSC is simple and exhibits high selectivity toward S2O82- anion in the presence of large interferences from other anions or cations. A fluorescence change from blue to green visualized under the UV light makes it possible to detect the persulfate anion with naked-eye. A mechanism underlying the molecular recognition has been explained from the 1H-NMR and single crystal X-ray structure experiments.

Solid-state photolysis of anthracene-linked ammonium salts: The search for topochemical anthracene photodimerizations

The reaction of 9-N,N-dimethylaminomethylanthracene 1 with aromatic carboxylic acids gave crystalline salts (2a, 2b, 3a and 3b), which were irradiated in the solid state. Whereas salt 3a was selectively transformed to the dimer 4a, the other salts were ph

Anthryl-1,2,4-oxadiazole-substituted calix[4]arenes as highly selective fluorescent chemodosimeters for Fe3+

Fluorescent chemosensors 1 and 2, with 1,2,4-oxadiazoles as the binding ligands and anthracene as the fluorophore, were synthesized through sequential 1,3-dipolar cycloaddition reactions of 25,27-dioxyacetonitrilecalix[4]arenes 8 and 11. The fluorescence

Photolysis of an Amphiphilic Assembly by Calixarene-Induced Aggregation

Photosensitizers generally show great tendency for self-aggregation in aqueous media, leading to quenched fluorescence and lower photosensitizing ability. Herein, we report that amphiphilic anthracene is highly photoreactive after aggregation induced by p-sulfonatocalix[4]arene in water. The formation of a host-guest supramolecular assembly and the photolysis of the anthryl core are identified by UV-vis and NMR spectroscopy, dynamic light scattering, and transmission electron microscopy. Additionally, the assembly exhibited efficient photolysis with visible light in the presence of exogenous photosensitizers. This approach could be extended to various photoresponsive self-assemblies and applications in phototherapy and the design of photodegradable materials. (Chemical Equation Presented)

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Reactivity of 9-anthracenecarboxylate in the presence of Mn(II) and Mn(III) ions: Biomimetic aerobic oxidative decarboxylation catalysed by a manganese(III) 2,2′-bipyridine complex

The stability of the 9-anthracenecarboxylate (AnthCO2–) in the presence of manganese ions and 2,2′-bipyridine (bpy) was explored. Two Mn(II) species were isolated: a one-dimensional system [Mn(bpy)(AnthCO2)2]n (1) and a dinuclear [{Mn(bpy)(AnthCO2)}2(μ-OH2)(μ-AnthCO2)2] compound (2), which was characterized by X-ray diffraction. Compound 2 can be obtained by hydrolysis of 1. These compounds present a specific electron paramagnetic resonance (EPR) signature and weak antiferromagnetic coupling, which is slightly stronger for the dinuclear complex (?4.8 cm?1) than for the chain (?1.3 cm?1). In the presence of Mn(III) ions AnthCO2– is not stable for long time. From the Mn(III) solution obtained by a comproportionation reaction between Mn(II) and Mn(VII) salts, first, a tetranuclear [Mn4(μ-AnthCO2)6(μ-O)2(bpy)2(ClO4)2] compound was isolated, showing the antiferromagnetic properties typical of a butterfly [Mn4O2]8+ core (J1 = ?41.0 cm?1, J2 = ?8.4 cm?1, J3 = ?10.6 cm?1 and DMn = ?3.7 cm?1). After that, the solution became yellow due to the reduction of the Mn(III) complex to a Mn(II) complex, and the decarboxylation and oxidation of the AnthCO2– ligand. This oxidation can lead to different compounds, depending on the reaction conditions (temperature and amount of O2): an ester, derived from the AnthCO2– and the intermediate 10-hydroxyanthrone, and the 9,10-anthraquinone.

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Synthesis, structural elucidation, and catalytic activity of bimetallic rhenium-tin complexes containing Schiff base ligand

Novel bimetallic systems with Re and Sn metals, containing Schiff base linker were designed and explored for their cooperative effect in the catalysis. ReSn bimetallic complexes were prepared by adopting a two-step synthesis procedure, which includes cova

Cu2O-CuO/Chitosan Composites as Heterogeneous Catalysts for Benzylic C?H Oxidation at Room Temperature

Recently, in catalysis, chitosan has been exploited as a macrochelating ligand for metal active species due to the presence of various functional groups in its structure. Moreover, copper-based catalysts are classified as one of the most environmentally friendly catalytic systems and their use for the oxidation of alkylarene has not been established much. Therefore, in this work, the hydrothermal synthesis of copper oxide-chitosan composites as heterogeneous catalysts for the benzylic C?H oxidation of alkylarene was investigated. Characterization results reveal mixed phases of CuO and Cu2O, inferring the ability of chitosan to act as a reducing sugar under the hydrothermal condition. The pre-existing interaction between copper species and chitosan as well as the co-existence of the Cu2O and CuO structures give rise to the efficient performance of the catalysts. The synthesized composites exhibit high activity for the oxidation of fluorene to 9-fluorenone at room temperature and small catalyst loading (1 mol % of Cu, >90 % conversion and 100 % selectivity). Superior TOF was observed, and a good scope of substrates can be converted to corresponding ketones in 48–97 % yields with these copper oxide-chitosan catalysts. In addition, the catalysts can be used for up to nine cycles without significant decrease of the activity.