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1,4-DIHYDROXYANTHRAQUINONE
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Name

1,4-DIHYDROXYANTHRAQUINONE

 EINECS 201-368-7
CAS No. 81-64-1 Density 1.54 g/cm3
PSA 74.60000 LogP 1.87320
Solubility <1 g/L (20 °C) in water Melting Point 198-199 °C(lit.)
Formula C14H8O4 Boiling Point 465.3 °C at 760 mmHg
Molecular Weight 240.215 Flash Point 249.3 °C
Transport Information N/A Appearance orange to red-brown crystalline powder
Safety 22-24/25-36/37-26 Risk Codes 36/37/38-43
Molecular Structure Molecular Structure of 81-64-1 (1,4-DIHYDROXYANTHRAQUINONE) Hazard Symbols IrritantXi
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;

Article Data 141

1,4-DIHYDROXYANTHRAQUINONE 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;

1,4-DIHYDROXYANTHRAQUINONE Chemical Properties

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

1,4-DIHYDROXYANTHRAQUINONE 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.

1,4-DIHYDROXYANTHRAQUINONE 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 .

1,4-DIHYDROXYANTHRAQUINONE Consensus Reports

Reported in EPA TSCA Inventory.

1,4-DIHYDROXYANTHRAQUINONE 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.

1,4-DIHYDROXYANTHRAQUINONE 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.

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