Product Name

  • Name

    1,8-Dihydroxyanthraquinone

  • EINECS 204-173-5
  • CAS No. 117-10-2
  • Article Data56
  • CAS DataBase
  • Density 1.541 g/cm3
  • Solubility insoluble in water
  • Melting Point 191-193 °C
  • Formula C14H8O4
  • Boiling Point 452.667 °C at 760 mmHg
  • Molecular Weight 240.215
  • Flash Point 241.691 °C
  • Transport Information
  • Appearance orange-brown or brown powder
  • Safety 36/37-22
  • Risk Codes 40
  • Molecular Structure Molecular Structure of 117-10-2 (1,8-Dihydroxyanthraquinone)
  • Hazard Symbols HarmfulXn
  • Synonyms Anthraquinone,1,8-dihydroxy- (8CI);1,8-Dihydroxy-9,10-anthracenedione;1,8-Dihydroxy-9,10-anthraquinone;1,8-Dioxyanthraquinone;Antrapurol;Chrysazin;Danthron;Danthrone;Diaquone;Laxanorm;Laxanthreen;
  • PSA 74.60000
  • LogP 1.87320

Synthetic route

1,8-diacetoxy-9,10-anthraquinone
1963-82-2

1,8-diacetoxy-9,10-anthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With water; trifluoroacetic acid at 65℃; for 1h;100%
1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone)
69043-83-0

1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone)

A

1,5-dihydroxyanthraquinone
117-12-4

1,5-dihydroxyanthraquinone

B

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With pyrrolidine In toluene for 1.5h; Heating;A 93%
B n/a
1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione
1432067-68-9

1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione
1432067-84-9

1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione

Conditions
ConditionsYield
With iron (III) perchlorate monohydrate In dichloromethane for 2h;A n/a
B 90%
With copper(II) perchlorate hexahydrate In dichloromethane for 2h;A n/a
B 70%
4-hydroxy-10-imino-5-methoxymethoxy-10H-anthracen-9-one
577975-52-1

4-hydroxy-10-imino-5-methoxymethoxy-10H-anthracen-9-one

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; methanol at 20℃; for 96h;86%
1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione
1182282-39-8

1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

2,10-dimethyl-6,12-dihydroanthra[1,2-b:8,7-b']difuran-6,12-dione

2,10-dimethyl-6,12-dihydroanthra[1,2-b:8,7-b']difuran-6,12-dione

Conditions
ConditionsYield
With iron at 160℃; for 0.0666667h; Claisen Rearrangement; Ionic liquid;A 16%
B 73%
1-hydroxy-8-(prop-2'-ynyloxy)anthraquinone
1393091-17-2

1-hydroxy-8-(prop-2'-ynyloxy)anthraquinone

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

10-hydroxy-2-methyl-6,11-dihydroanthra[1,2-b]furan-6,11-dione

10-hydroxy-2-methyl-6,11-dihydroanthra[1,2-b]furan-6,11-dione

Conditions
ConditionsYield
With iron at 160℃; for 0.2h; Claisen Rearrangement; Ionic liquid;A 15%
B 73%
8-Hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydro-anthraquinone
84399-87-1

8-Hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydro-anthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid67%
1,1-ethylenedioxy-6-hydroxy-1,4,4α,9aα-tetrahydro-9,10-anthraquinone
78526-20-2

1,1-ethylenedioxy-6-hydroxy-1,4,4α,9aα-tetrahydro-9,10-anthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With acetic acid at 100℃; for 0.333333h;40%
3-Hydroxy-2-(2-hydroxybenzoyl)-benzoesaeure
89646-25-3

3-Hydroxy-2-(2-hydroxybenzoyl)-benzoesaeure

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; sulfur trioxide; boric acid at 120℃; for 0.5h;38.4%
With boron trioxide; sulfuric acid at 100℃;
1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one

1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

1',8',10'-trihydroxy-8-(methoxymethoxy)-[2,10'-bianthracene]-1,4,9'(10'H)-trione

1',8',10'-trihydroxy-8-(methoxymethoxy)-[2,10'-bianthracene]-1,4,9'(10'H)-trione

Conditions
ConditionsYield
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 26h; Inert atmosphere;A n/a
B 34%
1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one

1',8',10'-trihydroxy-1,8-bis(methoxymethoxy)-[2,10'-bianthracen]-9'(10'H)-one

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

1',8',10'-trihydroxy-[2,10'-bianthracene]-1,4,5,8,9'(10'H)-pentaone

1',8',10'-trihydroxy-[2,10'-bianthracene]-1,4,5,8,9'(10'H)-pentaone

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid In water at 20℃; for 1.5h;A n/a
B 23%
1-hydroxy-8-methoxyanthraquinone
5539-66-2

1-hydroxy-8-methoxyanthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With hydrogen bromide; acetic acid
1,2-diamino-9,10-anthraquinone
1758-68-5

1,2-diamino-9,10-anthraquinone

A

1,5-dihydroxyanthraquinone
117-12-4

1,5-dihydroxyanthraquinone

B

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 90 - 120℃;
1,8-anthraquinonedisulphonic acid
82-48-4

1,8-anthraquinonedisulphonic acid

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With potassium carbonate
With quicklime; water at 180 - 200℃;
With calcium hydroxide; calcium chloride at 195 - 200℃; Darstellung; im Autoklaven;
1,8-dihydroxy-3-carboxy-anthraquinone
478-43-3

1,8-dihydroxy-3-carboxy-anthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1,8-dinitroanthraquinone
129-39-5

1,8-dinitroanthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With potassium acetate; acetic acid at 170℃;
Multi-step reaction with 2 steps
1: water; alkali sulfite
2: quicklime; water / 180 - 200 °C
View Scheme
With pyridine
With quicklime; water at 190 - 200℃;
2,4,5,7-tetraamino-1,8-dihydroxy-anthraquinone

2,4,5,7-tetraamino-1,8-dihydroxy-anthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With mixture of gaseous nitrogen oxides; sulfuric acid Erwaermen das Diazoniumsulfat mit Alkohol auf 60grad;
3-Bromojuglone
52431-65-9

3-Bromojuglone

1-<(trimethylsilyl)oxy>-1-methoxy-1,3-butadiene
110362-30-6

1-<(trimethylsilyl)oxy>-1-methoxy-1,3-butadiene

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With hydrogenchloride 1) THF, -78 deg C, 6 h, 2) -78 deg C to r.t., 2 h; Yield given. Multistep reaction;
1,8-dihydroxy-9(10H)-anthracenone
1143-38-0

1,8-dihydroxy-9(10H)-anthracenone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With oxygen In methanol for 1.5h; Rate constant; Mechanism; different pH; half lives of decomposition;
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;
With pyridinum sulfonate fluorochromate for 0.0222222h; Neat (no solvent); Microwave irradiation;
1,8-dihydroxy-9(10H)-anthracenone
1143-38-0

1,8-dihydroxy-9(10H)-anthracenone

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

1,8,1',8'-tetrahydroxy-10,10'-bianthrone
31991-54-5

1,8,1',8'-tetrahydroxy-10,10'-bianthrone

Conditions
ConditionsYield
With tetraphenylporphyrine; oxygen In methanol at -10℃; for 4h; Product distribution; Irradiation; other reagents, other solvents, other temp., no irradiation; inhibition by β-carotene;A 67 % Chromat.
B 19 % Chromat.
With 4-hydroxy-TEMPO benzoate; oxygen In dimethyl sulfoxide at 20℃; Kinetics; Further Variations:; Reagents;
1,8-dihydroxy-9(10H)-anthracenone
1143-38-0

1,8-dihydroxy-9(10H)-anthracenone

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

1,8,1',8'-tetrahydroxy-10,10'-bianthrone
31991-54-5

1,8,1',8'-tetrahydroxy-10,10'-bianthrone

C

1,8,10-Trihydroxy-9-anthron
64817-79-4

1,8,10-Trihydroxy-9-anthron

Conditions
ConditionsYield
With salcomine; oxygen In dichloromethane for 1h; Product distribution; Mechanism; in the dark; further complexes of transition metals, other solvents;
1,8,9,10-anthracenetetrol
59945-68-5

1,8,9,10-anthracenetetrol

1,8-dihydroxy-9,10-anthraquinone semiquinone
121151-81-3

1,8-dihydroxy-9,10-anthraquinone semiquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
In isopropyl alcohol Rate constant; Equilibrium constant;
10-bromo-1,8-dihydroxy-9(10H)-anthracenone
2891-30-7

10-bromo-1,8-dihydroxy-9(10H)-anthracenone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With rac-cysteine
1,8-dihydroxy-10-(1'-oxobutyl)-9(10H)-anthracenone
75464-11-8

1,8-dihydroxy-10-(1'-oxobutyl)-9(10H)-anthracenone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With oxygen In methanol for 1.5h; Rate constant; Mechanism; different pH; half lives of decomposition;
(4α,4aβ,9aβ)-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone
84399-87-1

(4α,4aβ,9aβ)-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran Ambient temperature;1.4 mg
1-Amino-4,5-dihydroxy-9,10-anthracenedione
78112-67-1

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

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sodium hydroxide; hypophosphorous acid; sodium nitrite 1.) water, dioxan, 2.) 0 deg C, 20 min; 70 deg C, 2 h; room temperature, 10 h; Multistep reaction;
(E)-1,8-dihydroxy-10-(1-oxo-3-phenyl-2-propenyl)-9(10H)-anthracenone

(E)-1,8-dihydroxy-10-(1-oxo-3-phenyl-2-propenyl)-9(10H)-anthracenone

A

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

B

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;
1,8-dihydroxy-10-(1-oxo-2-phenylethy)-9(10H)-anthracenone
151562-41-3

1,8-dihydroxy-10-(1-oxo-2-phenylethy)-9(10H)-anthracenone

A

phenylacetic acid
103-82-2

phenylacetic acid

B

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;
1,8-Dihydroxy-10-(1-oxo-3-phenylpropyl)-9(10H)-anthracenone
151562-48-0

1,8-Dihydroxy-10-(1-oxo-3-phenylpropyl)-9(10H)-anthracenone

A

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

Conditions
ConditionsYield
With oxygen In ethanol at 25℃; for 240h; Mechanism; other solvent; determinations of half-lives;
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

propionyl chloride
79-03-8

propionyl chloride

Propionic acid 9,10-dioxo-8-propionyloxy-9,10-dihydro-anthracen-1-yl ester

Propionic acid 9,10-dioxo-8-propionyloxy-9,10-dihydro-anthracen-1-yl ester

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

C36H36O6

C36H36O6

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1,8-bis(methoxymethoxy)-9,10-anthraquinone
134112-14-4

1,8-bis(methoxymethoxy)-9,10-anthraquinone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform for 16h; Heating;100%
With N-ethyl-N,N-diisopropylamine In chloroform; acetic acid methyl ester for 40h; Reflux;99%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

acetyl chloride
75-36-5

acetyl chloride

1,8-diacetoxy-9,10-anthraquinone
1963-82-2

1,8-diacetoxy-9,10-anthraquinone

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
With pyridine87%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

butyryl chloride
141-75-3

butyryl chloride

Butyric acid 8-butyryloxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Butyric acid 8-butyryloxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

acetic anhydride
108-24-7

acetic anhydride

1,8-diacetoxy-9,10-anthraquinone
1963-82-2

1,8-diacetoxy-9,10-anthraquinone

Conditions
ConditionsYield
With sodium acetate Reflux;98%
at 170℃;
With sodium acetate
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

bis(1,8-dihydroanthraquinonato)dicopper(II)
83533-69-1

bis(1,8-dihydroanthraquinonato)dicopper(II)

Conditions
ConditionsYield
In ethanol mixture was boiled for 10 min, left stirring for 1 h at room temp.; ppt. was filtered, washed several times with ethanol, acetone, finally diethyl ether, dried in vac. over P2O5; elem. anal.;98%
lead(II) nitrate

lead(II) nitrate

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

water
7732-18-5

water

lead 1,8-dihydroxyanthraquinone monohydride

lead 1,8-dihydroxyanthraquinone monohydride

Conditions
ConditionsYield
With sodium hydroxide at 70℃; for 2h; pH=9; Reagent/catalyst; Temperature;97.8%
diethyl sulfate
64-67-5

diethyl sulfate

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1,8-diethoxyanthracene-9,10-dione
16294-26-1

1,8-diethoxyanthracene-9,10-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;97%
With potassium carbonate; acetone
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

11-hydroxy-2-(2-hydroxyethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one
858519-37-6

11-hydroxy-2-(2-hydroxyethyl)anthra[9,1-de][1,3]oxazin-7(2H)-one

Conditions
ConditionsYield
With pyridine; copper(I) bromide at 20 - 80℃;97%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

1,8-dimethoxy-9,10-anthracenedione
6407-55-2

1,8-dimethoxy-9,10-anthracenedione

Conditions
ConditionsYield
With sodium carbonate at 320℃; for 0.0833333h;95%
With sodium carbonate In 1,2-dichloro-benzene Heating;87%
With sodium carbonate In various solvent(s) Yield given;
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

benzyl bromide
100-39-0

benzyl bromide

1-(benzyloxy)-8-hydroxyanthracene-9,10-dione
22516-60-5

1-(benzyloxy)-8-hydroxyanthracene-9,10-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; butanone for 15h; Reflux;94.8%
With potassium carbonate In N,N-dimethyl-formamide; butanone for 20h; Inert atmosphere; Reflux;
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

acetic anhydride
108-24-7

acetic anhydride

8-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate
43101-75-3

8-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl acetate

Conditions
ConditionsYield
With boric acid at 90℃; for 21h;94%
With boric acid at 95℃; for 5h;94%
With boric acid at 90℃;
With water; boric acid 1) 90 deg C, 10 h 2) room temp., 1 h; Yield given. Multistep reaction;
With boron trioxide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid 1) 3 h, 110 deg C; 2) 3 h; Yield given. Multistep reaction;
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 45h; Reflux; Inert atmosphere;94%
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 1.25h; silylation;73%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1,8-dihydroxy-9(10H)-anthracenone
1143-38-0

1,8-dihydroxy-9(10H)-anthracenone

Conditions
ConditionsYield
93.7%
With hydrogenchloride; acetic acid; tin(ll) chloride In water at 60 - 65℃; for 3h;92%
With hydrogenchloride; tin(ll) chloride In acetic acid Heating;90%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
77377-52-7

N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide

1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

1,8-bis((tert-butyldimethylsilyl)oxy)-9,10-anthraquinone

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In acetonitrile at 80℃; for 0.333333h; silylation;93%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

1-hydroxy-8-methoxyanthraquinone
5539-66-2

1-hydroxy-8-methoxyanthraquinone

Conditions
ConditionsYield
With sodium carbonate In various solvent(s) for 2h; Heating;93%
With sodium carbonate In various solvent(s) at 120℃; for 2h;81%
With sodium carbonate75%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

dimethyl sulfate
77-78-1

dimethyl sulfate

1,8-dimethoxy-9,10-anthracenedione
6407-55-2

1,8-dimethoxy-9,10-anthracenedione

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Heating;92%
With potassium carbonate In acetone for 24.5h; Reflux; Inert atmosphere;90%
Stage #1: 1,8-dihydroxy-9,10-anthracenedione With potassium carbonate In acetone Reflux;
Stage #2: dimethyl sulfate In acetone for 54h; Reflux;
85%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate
1018327-05-3

diethyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate

Conditions
ConditionsYield
With triphenylphosphine In toluene for 24h; Heating;92%
copper(II) choride dihydrate

copper(II) choride dihydrate

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

C28H14CuO8*2H2O

C28H14CuO8*2H2O

Conditions
ConditionsYield
Stage #1: copper(II) choride dihydrate; 1,8-dihydroxy-9,10-anthracenedione In methanol at 60℃; for 1h;
Stage #2: With potassium hydroxide In methanol for 4h; Reflux;
91.7%
Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

di-tert-butyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate
1018327-07-5

di-tert-butyl 2-(9,10-dihydro-1,8-dihydroxy-9,10-dioxo-anthracen-2-yl)fumarate

Conditions
ConditionsYield
With triphenylphosphine In toluene for 24h; Heating;91%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

propargyl bromide
106-96-7

propargyl bromide

1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione
1182282-39-8

1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;91%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;89%
With sodium carbonate In N,N-dimethyl-formamide at 20℃;88%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1-dodecylbromide
143-15-7

1-dodecylbromide

C38H56O4
1429868-49-4

C38H56O4

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide; acetone for 120h; Inert atmosphere; Reflux;91%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

allyl bromide
106-95-6

allyl bromide

A

10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone

10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone

B

9-[1-(prop-2-enyl)]-1,8,9-trihydroxy-10(9H)-anthracenone

9-[1-(prop-2-enyl)]-1,8,9-trihydroxy-10(9H)-anthracenone

Conditions
ConditionsYield
With indium; water In tetrahydrofuran; methanol at 30 - 32℃; Barbier allylation;A 90%
B 4%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

allyl bromide
106-95-6

allyl bromide

10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone

10-[1-(prop-2-enyl)]-1,8,10-trihydroxy-9(10H)-anthracenone

Conditions
ConditionsYield
With indium In tetrahydrofuran; methanol; water at 29.85 - 31.85℃;90%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

10-[(2,4-dinitrophenyl)hydrazono]-1,8-dihydroxy-10H-anthracen-9-one
156383-28-7

10-[(2,4-dinitrophenyl)hydrazono]-1,8-dihydroxy-10H-anthracen-9-one

Conditions
ConditionsYield
With sulfuric acid In methanol at 50℃; for 0.5h;90%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

bis(1,8-dihydroanthraquinonato)copper(II)
109837-65-2, 109837-66-3, 58806-62-5

bis(1,8-dihydroanthraquinonato)copper(II)

Conditions
ConditionsYield
In ethanol 1,8-DHAQ was dissolved in abs. ethanol, warmed to boiling, filtered, slow addn. of ethanolic soln. of Cu(CH3COO)2*H2O, mixture was stirred at room temp. for 1 h, kept in refrigerator overnight; ppt. was washed with ethanol, acetone, finally diethyl ether, dried in vac. over P2O5; elem. anal.;90%
1,8-dihydroxy-9,10-anthracenedione
117-10-2

1,8-dihydroxy-9,10-anthracenedione

1,8-dihydroxy-9,10-dihydroanthracene
64817-82-9

1,8-dihydroxy-9,10-dihydroanthracene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4.25h; Reflux;90%
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran Cooling with ice; Reflux;80%
With water; sodium hydroxide; zinc
With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran Reflux;
Multi-step reaction with 2 steps
1.1: acetic acid; potassium iodide; iodine / 2 h / 80 °C / Large scale
1.2: 8.5 h / 85 - 115 °C / Large scale
2.1: sodium tetrahydroborate; trifluoroacetic acid / tert-butyl methyl ether / -15 °C / Reflux
View Scheme

1,8-Dihydroxyanthraquinone Uses

The major use of 1,8-Dihydroxyanthraquinone (117-10-2) is as an intermediate in the production of alizarin and indanthrene dyestuffs.

1,8-Dihydroxyanthraquinone Consensus Reports

NTP 10th Report on Carcinogens. Reported in EPA TSCA Inventory.

1,8-Dihydroxyanthraquinone Specification

The 1,8-Dihydroxyanthraquinone, with the CAS registry number 117-10-2, is also known as 1,8-Dihydroxy-9,10-anthraquinone. It belongs to the product categories of Intermediates of Dyes and Pigments; Anthraquinones; Hydroxyanthraquinones; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 204-173-5. This chemical's molecular formula is C14H8O4 and molecular weight is 240.21. What's more, its IUPAC name is called 1,8-Dihydroxyanthracene-9,10-dione. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 1,8-Dihydroxyanthraquinone are: (1)ACD/LogP: 4.003; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.93; (4)ACD/LogD (pH 7.4): 2.43; (5)ACD/BCF (pH 5.5): 551.84; (6)ACD/BCF (pH 7.4): 17.35; (7)ACD/KOC (pH 5.5): 3049.70; (8)ACD/KOC (pH 7.4): 95.86; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 74.6 Å2; (13)Index of Refraction: 1.733; (14)Molar Refractivity: 62.432 cm3; (15)Molar Volume: 155.926 cm3; (16)Polarizability: 24.75×10-24cm3; (17)Surface Tension: 79.282dyne/cm; (18)Density: 1.541 g/cm3; (19)Flash Point: 241.691 °C; (20)Enthalpy of Vaporization: 73.928 kJ/mol; (21)Boiling Point: 452.667 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 1,8-Dihydroxyanthraquinone: this chemical can be prepared by 3-hydroxy-2-salicyloyl-benzoic acid. This reaction needs reagent H2SO4 at temperature of 120 °C. The reaction time is 30 min. The yield is 38.4 %.

1,8-Dihydroxyanthraquinone can be prepared by 3-hydroxy-2-salicyloyl-benzoic acid.

Uses of 1,8-Dihydroxyanthraquinone: (1) it is used as a stimulant laxative and used as intermediates in the production of alizarin and indanthrene dyestuffs; (2) it is used to produce other chemicals. For example, it can react with sulfuric acid dimethyl ester to get 1,8-dimethoxy-anthraquinone. The reaction occurs with reagent K2CO3 and other condition of heating for 48 hours. The yield is 77 %.

1,8-Dihydroxyanthraquinone can react with sulfuric acid dimethyl ester to get 1,8-dimethoxy-anthraquinone.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it has limited evidence of a carcinogenic effect. Therefore, you should wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1) SMILES: c1cc2c(c(c1)O)C(=O)c3c(cccc3O)C2=O
(2) InChI: InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
(3) InChIKey: QBPFLULOKWLNNW-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous > 10gm/kg (10000mg/kg)   Pharmacology and Toxicology Vol. 61, Pg. 153, 1987.
mouse LD50 oral > 7gm/kg (7000mg/kg)   Drug and Chemical Toxicology. Vol. 1, Pg. 89, 1977/1978.
rat LD50 intraperitoneal 1110mg/kg (1110mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 52(12), Pg. 93, 1987.

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