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81-64-1

Basic Information
CAS No.: 81-64-1
Name: 1,4-DIHYDROXYANTHRAQUINONE
Molecular Structure:
Molecular Structure of 81-64-1 (1,4-DIHYDROXYANTHRAQUINONE)
Formula: C14H8O4
Molecular Weight: 240.21
Synonyms: Anthraquinone,1,4-dihydroxy- (8CI);1,4-Dihydroxy-9,10-anthracenedione;1,4-Dihydroxy-9,10-anthraquinone;1,4-Dihydroxyanthraquinone;C.I. 58050;C.I.Solvent Orange 100;C.I. Solvent Orange 86;Chinizarin;Macrolex OrangeGG;NSC 15367;NSC 229036;NSC 40899;NSC 646569;Quinizarin;Quinizarine;Smoke Orange 18;Smoke Orange R;Solvent Orange 100;Solvent Orange 86;
EINECS: 201-368-7
Density: 1.54 g/cm3
Melting Point: 198-199 °C(lit.)
Boiling Point: 465.3 °C at 760 mmHg
Flash Point: 249.3 °C
Solubility: <1 g/L (20 °C) in water
Appearance: orange to red-brown crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-43
Safety: 22-24/25-36/37-26
Transport Information:
PSA: 74.60000
LogP: 1.87320
Synthetic route
100073-85-6

N-(p-tolyl)-1,4-dihydroxy-9,10-anthraquinone 9-imine

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 1h;100%

9a-chloro-5,8-dihydroxy-1-trimethylsilyloxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With pyridine In chloroform for 48h; Ambient temperature;100%
17648-03-2

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With nitric acid; bentonite for 0.166667h; Product distribution; Further Variations:; Reagents; reaction times; types of irradiation; Oxidation; Irradiation;100%
With sodium hydroxide; oxygen
6119-74-0

1,4-dimethoxyanthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78℃; for 0.166667h;100%
33266-08-9

1,4-dibenzoyloxy-9,10-anthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With water; trifluoroacetic acid at 72℃; for 0.0833333h;99%
2289-36-3

1,4-diacetoxy-9,10-anthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With water; trifluoroacetic acid at 72℃; for 0.0833333h;96%
Multi-step reaction with 2 steps
1: 4 percent / alkali-metal alcoholate / 70 °C
2: 91 percent / conc. aq. HCl / ethanol / 1 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium isopropoxide / propan-2-ol / 0.5 h / 70 °C
2: 100 percent / conc. H2SO4 / 1 h / 20 °C
View Scheme
With lipase supported in poly(methylmethacrylate) beads; water In cyclohexane at 24.84℃; Enzymatic reaction;
85-44-9

phthalic anhydride

106-48-9

4-chloro-phenol

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; boric acid at 190 - 225℃; for 5h;94%
With fuming sulphuric acid; boric acid at 25℃; for 11h; Temperature; Solvent; Concentration; Reagent/catalyst;90%
With sulfuric acid; boric acid at 200℃; for 3.5h;85%
98771-41-6

9,10-di(p-tolylamino)-1,4-anthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 1h; Heating;91%
1709-63-3

anthracene-1,4,9,10-tetraone

107-15-3

ethylenediamine

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

20269-39-0

6-hydroxy-1,2,3,4-tetrahydronaphtho<2,3-f>quinoxaline-7,12-dione

Conditions
ConditionsYield
In pyridine Ambient temperature;A 1.2%
B 90.7%
In pyridine at 30℃; for 6h;A 1.2%
B 90.7%
1709-63-3

anthracene-1,4,9,10-tetraone

24454-89-5

2-acetoxy-1,3-butadiene

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

63229-39-0

2-acetoxy-1,4,4a,12a-tetrahydronaphthacene-5,6,11,12-tetrone

C

Acetic acid 9,10,11,14-tetraoxo-1,4,9,10-tetrahydro-4a,9a-[2]buteno-anthracen-2-yl ester

Conditions
ConditionsYield
In benzene at 55℃; for 96h;A n/a
B 83%
C n/a
In benzene at 55℃; for 96h; Title compound not separated from byproducts;
475-38-7

5,8-Dihydroxy-1,4-naphthoquinone

123-73-9

crotonaldehyde

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With benzoic acid; L-proline In toluene at 50℃; for 5h; Inert atmosphere; Enzymatic reaction;82%
129-43-1

1-hydroxyanthraquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; boric acid for 5h; Irradiation;81%
With air; sulfuric acid Product distribution; Mechanism; Irradiation; without air (argon);
84-65-1

9,10-phenanthrenequinone

A

605-32-3

2-hydroxy-9,10-anthraquinone

B

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; boric acid for 5h; Product distribution; Mechanism; Irradiation; other time;A n/a
B 81%
85-44-9

phthalic anhydride

123-31-9

hydroquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With aluminium trichloride; sodium chloride at 165℃; for 4h; Fridel-Crafts acylation;80%
With sulfuric acid; boric acid at 200℃; for 3.5h;55%
With aluminum (III) chloride; sodium chloride at 165 - 170℃; for 0.75h; Friedel-Crafts Acylation;44%

1-hydroxy-4-fluoro-anthracene-9,10-dione

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sodium trimethylsilanolate In tetrahydrofuran Substitution; stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h;80%
28736-42-7

1,4-difluoroanthracene-9,10-dione

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation;78%
Multi-step reaction with 2 steps
1: 90 percent / NaOSi(CH3)3 / tetrahydrofuran / stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h
2: 80 percent / NaOSi(CH3)3 / tetrahydrofuran / stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h
View Scheme
88-95-9

Phthaloyl dichloride

150-78-7

1,4-dimethoxybezene

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With aluminium trichloride In nitrobenzene at 80℃; for 0.5h;72%
29525-00-6

2,3-dichloro-1,4-dihydroxyanthracene-9,10-dione

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
Stage #1: 2,3-dichloro-1,4-dihydroxyanthracene-9,10-dione With iron In acetic acid for 0.75h; Dehalogenation; reduction; Heating;
Stage #2: With oxygen In sodium hydroxide pH=8 - 9; Oxidation;
72%
84-65-1

9,10-phenanthrenequinone

A

605-32-3

2-hydroxy-9,10-anthraquinone

B

129-43-1

1-hydroxyanthraquinone

C

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid at 25℃; Irradiation;A 70%
B n/a
C n/a
With sulfuric acid at 25℃; Irradiation; prolonged irradiation;A n/a
B 55%
C 6%
106-48-9

4-chloro-phenol

88-99-3

benzene-1,2-dicarboxylic acid

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; boric acid at 230℃; for 0.166667h; Product distribution; Further Variations:; Temperatures; Reagents; reaction times; microwave powers; microwave irradiation;68.3%
123-31-9

hydroquinone

88-95-9

Phthaloyl dichloride

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With aluminium trichloride In nitrobenzene at 100℃; for 0.5h;65%
With aluminium trichloride; C6H4NO2 at 165℃; for 4h; Fridel-Crafts acylation;
51287-54-8

3-(phenylsulfanyl)isobenzofuran-1(3H)-one

106-51-4

p-benzoquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
Stage #1: 3-(phenylsulfanyl)isobenzofuran-1(3H)-one With lithium tert-butoxide In tetrahydrofuran at -60℃; for 0.416667h;
Stage #2: p-benzoquinone In tetrahydrofuran at -60 - 20℃; Hauser annulation; Further stages.;
56%
82-34-8

1-nitroanthraquinone

A

129-43-1

1-hydroxyanthraquinone

B

81-64-1

1,4-dihydroxy-9,10-anthracenedione

C

72-48-0

1,2-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With potassium hydroxide; Cumene hydroperoxide In dimethyl sulfoxide at 15 - 25℃; for 10h;A 55%
B 13%
C 32%
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 15 - 20℃; for 3h;A 45%
B 8%
C 35%
27613-27-0

3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile

106-51-4

p-benzoquinone

81-64-1

1,4-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
Stage #1: 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile With lithium tert-butoxide In tetrahydrofuran at -60℃; for 0.416667h;
Stage #2: p-benzoquinone In tetrahydrofuran at -60 - 20℃; Hauser annulation; Further stages.;
52%
67-56-1

methanol

41099-45-0

2,10-hydroxy-9-chloro-1,4-anthraquinone

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

7336-64-3

1-hydroxy-4-methoxyanthracene-9,10-dione

Conditions
ConditionsYield
With perchloric acid for 12h; Heating;A 36%
B 49%
38399-72-3

leuco-1,4-dihydroxyanthraquinone

15186-48-8

2,3-isopropylidene-glyceraldehyde

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

128885-71-2

dihydroxy-1,4 (hydroxy-3 propyl)-2 anthraquinone-9,10

C

111301-39-4

(-)-(S)<(dimethyl-2,2 dioxolanne-1,3 yl-4) methyl>-2 dihydroxy-1,4 anthraquinone-9,10

D

111301-40-7, 111331-26-1

<(dimethyl-2,2 dioxolanne-1,3 yl-4) hydroxymethyl>-2 dihydroxy-1,4 anthraquinone-9,10

Conditions
ConditionsYield
With potassium hydroxide; sodium hydrogensulfite Product distribution; 1.) MeOH, 15 min, 20 deg C, 2.) MeOH, 12 h, 20 deg C, further temperatures;A 33%
B 4%
C 22%
D 37%
79207-97-9

1,4-bis(prop-2'-enyloxy)-9,10-anthraquinone

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

79208-09-6

1,4-dihydroxy-2-(prop-2'-enyl)-9,10-anthraquinone

C

79208-01-8

2,3-diallyl-1,4-dihydroxyanthraquinone

D

79208-08-5

1-hydroxy-4-propanoyl-2-(prop-2'-enyl)anthraquinone

Conditions
ConditionsYield
In 1,2-dichloro-benzene for 25h; Heating;A 5%
B 32%
C 14%
D 18%
14569-45-0

5,8-diacetoxy-1,4-naphthoquinone

108030-46-2

(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

27573-16-6

5-nitro-1,4-dihydroxy-9,10-anthracenedione

C

117554-15-1

Acetic acid 4-hydroxy-5-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

D

117554-14-0

Acetic acid 4-hydroxy-8-nitro-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Conditions
ConditionsYield
In xylene for 24h; Ambient temperature;A 4.2%
B 30.2%
C n/a
D n/a
In xylene for 24h; Ambient temperature; Title compound not separated from byproducts;A 4.2%
B 30.2%
C n/a
D n/a
108030-46-2

(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene

475-38-7

5,8-Dihydroxy-1,4-naphthoquinone

A

81-64-1

1,4-dihydroxy-9,10-anthracenedione

B

27573-16-6

5-nitro-1,4-dihydroxy-9,10-anthracenedione

C

117554-13-9

2-(dimethylamino)-5,8-dihydroxynaphthalene-1,4-dione

Conditions
ConditionsYield
In xylene for 12h; Ambient temperature;A 9.2%
B 14.1%
C 24.9%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

106-95-6

allyl bromide

79207-97-9

1,4-bis(prop-2'-enyloxy)-9,10-anthraquinone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 16h;100%
With potassium carbonate In acetone for 48h; Reflux;89%
With tetraethylammonium bromide; potassium carbonate; sodium hydroxide at 85℃; for 0.5h; Microwave irradiation; Sealed tube;85%
With potassium carbonate In acetone Heating;81%
With potassium carbonate In acetone Reflux;
81-64-1

1,4-dihydroxy-9,10-anthracenedione

77-78-1

dimethyl sulfate

6119-74-0

1,4-dimethoxyanthraquinone

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 480h; Ambient temperature;99%
With potassium carbonate In acetone for 4h; Reflux;96%
With potassium carbonate In acetone for 72h; Heating;95%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

107-15-3

ethylenediamine

15077-66-4

6-hydroxy-1,2,3,4-tetrahydronaphtho[2,3-f]-quinoxaline-7,12-dione

Conditions
ConditionsYield
With [bmim]PF6; copper dichloride at 20℃; for 2h; Product distribution; Further Variations:; Reagents;99%
14285-68-8

decacarbonyldirhenium(0)

81-64-1

1,4-dihydroxy-9,10-anthracenedione

7128-64-5

Uvitex OB

918153-35-2

[(Re(CO)3)4(2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene)2(1,4-dihydroxy-9,10-anthraquinone(-2H))2]

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene under reflux;99%
34841-06-0

3-bromo-4-methoxybenzylaldehyde

81-64-1

1,4-dihydroxy-9,10-anthracenedione

2-((3-bromo-4-methoxyphenyl)(hydroxy)methyl)-1,4-dihydroxyanthracene-9,10-dione

Conditions
ConditionsYield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With potassium hydroxide In methanol; water for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: 3-bromo-4-methoxybenzylaldehyde With sodium dithionite In methanol; water Time;
99%
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium dithionite; potassium hydroxide In methanol; water for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: 3-bromo-4-methoxybenzylaldehyde In methanol; water at 0℃; for 4h; Inert atmosphere;
Stage #3: With dihydrogen peroxide In water for 0.333333h;
76%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

635-12-1

1,4-anthraquinone

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 24h; Heating;98%
With methanol; sodium tetrahydroborate at 0℃;98%
With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;97%
78-88-6

2,3-Dichloroprop-1-ene

81-64-1

1,4-dihydroxy-9,10-anthracenedione

72183-81-4

1,4-Bis-(2-chloro-allyloxy)-anthraquinone

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetone for 344h; Heating;98%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;
81-64-1

1,4-dihydroxy-9,10-anthracenedione

107-15-3

ethylenediamine

20269-39-0

6-hydroxy-1,2,3,4-tetrahydronaphtho<2,3-f>quinoxaline-7,12-dione

Conditions
ConditionsYield
copper dichloride In pyridine at 30℃; for 24h; Product distribution; Mechanism; further copper chloride catalyst, effect of oxygen without catalyst, further amine;98%
With copper dichloride In pyridine at 30℃; for 6h; Product distribution; other diamines, also in the absence of a copper salts;98%
copper dichloride In pyridine at 30℃; for 24h;98%
With oxygen; copper dichloride In pyridine at 30℃; for 6h;98%
With copper dichloride Ambient temperature;33%
476-60-8

leucoquinizarin

81-64-1

1,4-dihydroxy-9,10-anthracenedione

122-80-5

N-acetyl-p-phenylenediamine

C22H16N2O4

Conditions
ConditionsYield
Stage #1: N-acetyl-p-phenylenediamine With hydrogenchloride In water at 40 - 50℃; for 0.5h;
Stage #2: leucoquinizarin; 1,4-dihydroxy-9,10-anthracenedione In water at 85 - 90℃; Solvent; Temperature;
97.13%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

106-49-0

p-toluidine

128-80-3

D and C green 6

Conditions
ConditionsYield
With leucoquinizarin; boric acid; sodium hydrogensulfite In ethanol; benzene at 62 - 66℃; for 12h; Temperature; Solvent;97%
With 1-butyl-3-ethyl-1H-imidazolium tetrafluoroborate at 85 - 125℃; Reagent/catalyst; Temperature; Green chemistry; Large scale;95.9%
With boric acid; calcium carbonate; tin(ll) chloride at 110 - 130℃;
421-83-0

trifluoromethane sulfonyl chloride

81-64-1

1,4-dihydroxy-9,10-anthracenedione

96701-08-5

1,4-Bis-(trifluoromethanesulfonyloxy)-9,10-anthracenedione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate In dichloromethane at 5 - 10℃; for 0.5h;97%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

106-95-6

allyl bromide

10-[1-(prop-2-enyl)]-1,4,10-trihydroxy-9(10H)-anthracenone

Conditions
ConditionsYield
With indium; water In tetrahydrofuran; methanol at 30℃; Barbier allylation;97%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

106-94-5

propyl bromide

847901-15-9

1,4-dipropoxy-9,10-anthraquinone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Heating;97%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Williamson Ether Synthesis; Inert atmosphere;89%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

38399-72-3

leuco-1,4-dihydroxyanthraquinone

106-50-3

1,4-phenylenediamine

C20H14N2O3

Conditions
ConditionsYield
With boric acid In butan-1-ol for 16h; Reagent/catalyst; Reflux;97%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

17648-03-2

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione

Conditions
ConditionsYield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium carbonate In water at 85℃; Inert atmosphere;
Stage #2: With sodium dithionite In water Inert atmosphere;
96.1%
With sodium disulfite; potassium carbonate Hydrogenation;93%
With acetic acid; aluminium; indium(III) chloride In ethanol; water at 90℃; for 11h;78%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

silver nitrate

620591-70-0

C14H6(O)2(OAg)2

Conditions
ConditionsYield
With triethylamine In ethanol; triethylamine; acetonitrile byproducts: NEt3*HNO3; a soln. of quinone in Et3N and EtOH were added dropwise under N2 to a soln. of AgNO3 in MeCN-EtOH in the dark at 25°C, the mixt. was stirred for 2 h; filtd., ppt. was washed with cold EtOH, filtrate evapd. under vac.; elem. anal.;96%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

106-96-7

propargyl bromide

1045-75-6

1,4-bis(prop-2-ynyloxy)anthracene-9,10-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;96%
With potassium carbonate In acetone for 120h; Schlenk technique; Reflux;23%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

leuco-1,4-dihydroxyanthraquinone

Conditions
ConditionsYield
Stage #1: 1,4-dihydroxy-9,10-anthracenedione With sodium hydroxide In water at 70 - 75℃; for 0.5h;
Stage #2: With thiourea In water at 88℃; for 2h; Reagent/catalyst;
96%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

109-73-9

N-butylamine

17354-14-2

solvent blue 35

Conditions
ConditionsYield
With acetic acid; sodium sulfate In ethanol for 4h; Reflux;95.3%
With sodium dithionite; ethanol
81-64-1

1,4-dihydroxy-9,10-anthracenedione

74-89-5

methylamine

2475-44-7

disperse blue 14

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; tetrafluoroboric acid; bromobutyric acid In methanol at 50 - 55℃; Temperature; Large scale;95.1%
With ethanol; sodium carbonate; copper(II) sulfate at 140℃;
With sodium hydroxide; copper(II) sulfate at 140℃;
81-64-1

1,4-dihydroxy-9,10-anthracenedione

109-76-2

Trimethylenediamine

2-(3'-aminopropylamino)-1,4-dihydroxyanthraquinone

Conditions
ConditionsYield
copper dichloride In pyridine at 30℃; for 24h;95%
With oxygen; copper dichloride In pyridine at 30℃; for 6h;95%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

109-77-3

malononitrile

86092-18-4

2-amino-3-cyano-5-hydroxyanthra<1,2-b>furan-6,11-dione

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide Ambient temperature;95%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

74-88-4

methyl iodide

6119-74-0

1,4-dimethoxyanthraquinone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃;95%
With aluminum oxide; potassium fluoride In dimethyl sulfoxide at 35℃; for 10h;58.5%
With potassium carbonate In acetone Reflux;31.5%
81-64-1

1,4-dihydroxy-9,10-anthracenedione

13076-29-4

1,4-dimethoxyanthracene

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid In methanol95%
Multi-step reaction with 3 steps
1: 83 percent / K2CO3 / 1,2-dichloro-benzene / 1 h / Heating
2: 100 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C
3: 40 percent / HCl / tetrahydrofuran / 2 h / 40 °C
View Scheme
Multi-step reaction with 2 steps
1: K2CO3 / acetone
2: 62 percent / Zn; glacial acetic acid / 15 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / tetrahydrofuran / 24 h / Reflux
2: zinc; acetic acid / 96 h / Reflux
View Scheme
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  • High purity Quinizarine 81-64-1 /manufacturer/low price/high quality/in stock

  • Casno:

    81-64-1

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    81-64-1

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  • Casno:

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  • 1,4-Dihydroxyanthraquinone

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    81-64-1

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  • 1,4-Dihydroxyanthraquinone CAS 	81-64-1

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  • 1,4-DIHYDROXYANTHRAQUINONE

  • Casno:

    81-64-1

    1,4-DIHYDROXYANTHRAQUINONE

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  • 1,4-Dihydroxyanthraquinone

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Chemistry

IUPAC Name:1,4-dihydroxyanthracene-9,10-dione
Molecular Formula:C14H8O4
Molecular Weight:240.210920 g/mol
Appearance:red-brown powder
Melting Point:198-199 °C(lit.)
Boiling Point:450 °C
Flash Point:222 °C
vapor density:8.3 (vs air)
vapor pressure:1 mm Hg ( 196.7 °C)  
Colour Index:58050
Water Solubility:<1 g/L (20 oC)
Merck:14,8064
BRN:1914036
Synonyms of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
1,4-dihydroxy-9,10-anthracenedione;1,4-DIHYDROXYANTHRAQUINONE;1,4 DIHYROXY AQ;DSD ACID;CI NO 58050;CI 58050;LABOTEST-BB LT00052844;PIGMENT VIOLET 12
Categories of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Hydroxyanthraquinones;Solvent Dyestuff

Uses

1,4-DIHYDROXYANTHRAQUINONE(81-64-1) is an important dye intermediate used to make Disperse Blue HSR, Disperse Blue 5R, Disperse Blue B, scattered dark blue RB, anthraquinone acid blue R, brilliant blue RAW Weak Acid Green GS, to restore the gray BG, Vat Brown BR, etc.

Toxicity Data With Reference

1.   

eye-rbt 500 mg/24H MLD

   28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,102.
2.   

mmo-sat 100 µg/plate

   MUREAV    Mutation Research. 40 (1976),203.
3.   

ipr-rat LD50:2100 mg/kg

   GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 21 (12)(1977),27.
4.   

ivn-mus LD50:320 mg/kg

   CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#03274 .

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Hazard Codes:Xi
Risk Statements:36/37/38-43
36/37/38:Irritating to eyes, respiratory system and skin
43:May cause sensitization by skin contact   
Safety Statements:22-24/25-36/37-26
22:Do not breathe dust 
24/25:Avoid contact with skin and eyes 
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice   
WGK Germany:2
RTECS:CB6600000
Poison by intravenous route. Moderately toxic by intraperitoneal route. Mutation data reported. An eye irritant. A weak allergen. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

First Aid Measures of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.

Storage of 1,4-DIHYDROXYANTHRAQUINONE(81-64-1):
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.