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84-65-1

Basic Information
CAS No.: 84-65-1
Name: Anthraquinone
Molecular Structure:
Molecular Structure of 84-65-1 (Anthraquinone)
Formula: C14H8O2
Molecular Weight: 208.22
Synonyms: EPA Pesticide Chemical Code 122701;Hoelite;Morkit;Anthraquinone [BSI:ISO];9,10-Anthraquinone;9,10-Dioxoanthracene;Anthracene, 9,10-dihydro-9,10-dioxo-;Corbit;Anthradione;Bis-alkylamino anthraquinone;Anthrapel;9,10-Anthrachinon [Czech];9.10-Anthraquinone;anthra-9,10-quinone;anthracene-9,10-dione;Anthraquinone(AQ);
EINECS: 201-549-0
Density: 1.308 g/cm3
Melting Point: 284-286 °C(lit.)
Boiling Point: 377 °C at 760 mmHg
Flash Point: 141.4 °C
Solubility: water: <0.1 g/100 mL at 23 °C
Appearance: dull yellow powder
Hazard Symbols: IrritantXi
Risk Codes: 43-36/37/38
Safety: 36/37-37/39-26-24
Transport Information:
PSA: 34.14000
LogP: 2.46200
Synthetic route
613-31-0

9,10-dihydroanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
120-12-7

anthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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 acid100%
90-44-8

anthracen-9(10H)-one

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
58343-58-1

9,10-dihydro-9,10-dihydroxyanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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

A

624-92-0

Dimethyldisulphide

B

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With osmium(VIII) oxide; trimethylamine-N-oxide In tetrahydrofuran; pyridine; water at 65℃;100%
100622-34-2

anthracene-9-boronic acid

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst;99.03%
2395-97-3

9,10-dimethoxyanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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
2444-68-0

9-vinylanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; for 72h;98%
106-99-0

buta-1,3-diene

123-31-9

hydroquinone

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
85-52-9

2-Benzoylbenzoic acid

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
642-31-9

9-anthracene aldehyde

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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;
37170-96-0

N-(anthracen-9-yl)acetamide

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With Selectfluor In methanol at 30℃; for 0.5h;97%
613-31-0

9,10-dihydroanthracene

[(C12H8N2)2Mn(μ-O)2Mn(C12H8N2)2](ClO4)4

A

100685-12-9, 463965-74-4

[(1,10-phenanthroline)2Mn(η1-OClO3)2]

B

120-12-7

anthracene

C

90-44-8

anthracen-9(10H)-one

D

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
93496-77-6

9,10-bromoanthracene-9-carbaldehyde

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
4741-24-6

9,10-epidioxy-9,10-dihydroanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 60℃;74%
1564-64-3

9-Bromoanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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
723-62-6

9-Anthracenecarboxylic acid

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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;
613-31-0

9,10-dihydroanthracene

A

120-12-7

anthracene

B

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
2395-96-2

9-methoxyanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With water; potassium bromide In chloroform at 25℃; pH=9; Electrochemical reaction;96%
667-91-4

10-benzhydrylidene-9-anthrone

A

119-61-9

benzophenone

B

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
123412-37-3

1-<<(4-fluorophenyl)sulfonyl>oxy>-9,10-anthraquinone

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With triethylammonium formate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In 1,4-dioxane at 90℃; for 0.5h; Product distribution;95%
1468-95-7

9-hydroxymethylanthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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

anthracene; phenanthrene; mixture of

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
53760-37-5

9,10-Diaminoanthrazene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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%
885-19-8

1,4-dihydro-9,10-anthraquinone

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
palladium on activated charcoal In toluene for 12h; Heating;94%
With air
63934-06-5

9-methoxyanthracene-10-carboxaldehyde

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
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

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 20℃; for 5h;94%
71440-45-4

9,10-dihydroanthracen-9,10-dicarbaldehyde

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether; iodosylbenzene In diethyl ether; dichloromethane at 20℃; for 2h;93%
28871-52-5

9,10-bis(trimethylsilyloxy)anthracene

84-65-1

9,10-phenanthrenequinone

Conditions
ConditionsYield
With lithium perchlorate In acetonitrile anode potential 1.0 V vs. SCE, graphite felt anode, 2.5 F mol-1;92%
84-65-1

9,10-phenanthrenequinone

4981-66-2

9,10-Dihydroxyanthracene

Conditions
ConditionsYield
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%
84-65-1

9,10-phenanthrenequinone

1143-50-6

5,6-dihydro-6,11-dioxomorphanthridine

Conditions
ConditionsYield
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%
84-65-1

9,10-phenanthrenequinone

138519-02-5

dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester

159638-86-5

bis[4,5-di(methylsulfanyl)-1,3-dithiol-2-ylidene]-9,10-dihydroanthracene

Conditions
ConditionsYield
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%
84-65-1

9,10-phenanthrenequinone

allylindium sesquiiodide

allylindium sesquiiodide

32501-68-1

10-[1-(prop-2-enyl)]-10-hydroxy-9(10H)-anthracenone

Conditions
ConditionsYield
In N,N-dimethyl-formamide at -23℃; for 3h;100%
17136-36-6

N-benzylglycine

84-65-1

9,10-phenanthrenequinone

N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one

Conditions
ConditionsYield
With formaldehyd In 1,4-dioxane; benzene for 3h; Reflux; Dean-Stark;100%
50-00-0

formaldehyd

17136-36-6

N-benzylglycine

84-65-1

9,10-phenanthrenequinone

N-benzyl-10H-spiro[anthracene-9,5′-oxazolidin]-10-one

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

sodium metaborate

84-65-1

9,10-phenanthrenequinone

sodium perborate hexahydrate

Conditions
ConditionsYield
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%
84-65-1

9,10-phenanthrenequinone

82-34-8

1-nitroanthraquinone

Conditions
ConditionsYield
In water; nitric acid99.2%
With phosphoric acid; sulfuric acid; nitric acid In tetrachloromethane for 6h; Ambient temperature;90%
With nitric acid In water71%
84-65-1

9,10-phenanthrenequinone

10303-96-5

9,10-bis(formamido)anthracene

Conditions
ConditionsYield
for 12h; Reflux;99%
84-65-1

9,10-phenanthrenequinone

613-31-0

9,10-dihydroanthracene

Conditions
ConditionsYield
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
ConditionsYield
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%
84-65-1

9,10-phenanthrenequinone

56-81-5

glycerol

82-05-3

7H-benz[d,e]anthracene-7-one

Conditions
ConditionsYield
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
84-65-1

9,10-phenanthrenequinone

82-49-5

1-anthraquinonesulfonic acid

Conditions
ConditionsYield
In nitric acid-treated palladium; sulfuric acid98%
With sulfuric acid; sulfur trioxide; mercury at 130℃;
With mercurosulfate; sulfuric acid; sulfur trioxide at 150℃;
84-65-1

9,10-phenanthrenequinone

132206-01-0

cis-11,12-Dicyano-9,10-ethano-9,10-dihydro-9,10-dihydroxyanthracene

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In pyridine for 2h;98%
84-65-1

9,10-phenanthrenequinone

62217-35-0

dimethyl 1,3-benzodithiol-2-ylphosphonate

69213-08-7

9,10-bis-(1,3-benzdithiol-2-ylidene)-9,10-dihydroanthracene

Conditions
ConditionsYield
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;
84-65-1

9,10-phenanthrenequinone

62-53-3

aniline

34863-09-7

N,N'-diphenylanthroquinonediimine

Conditions
ConditionsYield
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
84-65-1

9,10-phenanthrenequinone

73296-31-8

phenyltellurotrimethylsilane

28871-52-5

9,10-bis(trimethylsilyloxy)anthracene

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

Molecular Structure of Anthraquinone (CAS NO.84-65-1):

Molecular Formula: C14H8O2
Molecular Weight: 208.2121
IUPAC Name: Anthracene-9,10-dione
Synonyms of Anthraquinone (CAS NO.84-65-1): Anthraquinone [BSI:ISO] ; 9,10-Anthracenedione ; 9,10-Anthrachinon ; 9,10-Anthrachinon [Czech] ; 9,10-Anthraquinone ; 9,10-Dioxoanthracene ; AI3-09073 ; Anthracene, 9,10-dihydro-9,10-dioxo- ; Bis-alkylamino anthraquinone ; CCRIS 649 ; Caswell No. 052A ; Corbit ; EINECS 201-549-0 ; EPA Pesticide Chemical Code 122701 ; HSDB 2074 ; Hoelite ; Morkit ; NSC 7957
CAS NO: 84-65-1
Classification Code: Agricultural Chemical ; Avicide ; Mutation data ; TSCA Flag T [Subject to the Section 4 test rule under TSCA] ; Tumor data
Melting Point: 284-286 °C
Index of Refraction: 1.659
Molar Refractivity: 58.66 cm3
Molar Volume: 159 cm3
Surface Tension: 55.8 dyne/cm
Density: 1.308 g/cm3
Flash Point: 141.4 °C
Enthalpy of Vaporization: 62.47 kJ/mol
Boiling Point: 377 °C at 760 mmHg
Vapour Pressure: 6.97E-06 mmHg at 25°C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 37, 1991.
quail LD50 unreported > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C23, 1991.
rat LC50 inhalation > 1300mg/m3/4H (1300mg/m3)   Pesticide Manual. Vol. 9, Pg. 37, 1991.
rat LD50 intraperitoneal 3500mg/kg (3500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(12), Pg. 27, 1977.
rat LD50 skin > 1gm/kg (1000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A019, Pg. 1983,
rat LDLo oral 15gm/kg (15000mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 22, 1982.

Consensus Reports

 Anthraquinone (CAS NO.84-65-1) is reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes of Anthraquinone (CAS NO.84-65-1): IrritantXi
Risk Statements: 43-36/37/38 
R43: May cause sensitization by skin contact. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-39-26-24 
S36/37: Wear suitable protective clothing and gloves. 
S39: Wear eye / face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S24: Avoid contact with skin.
WGK Germany: 1
RTECS: CB4725000

Specification

1. Fire Fighting Measures 
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.  Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
2. Handling and Storage 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Store in a tightly closed container.