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| CAS No.: | 72-48-0 |
|---|---|
| Name: | 1,2-Dihydroxy-9,10-anthracenedione |
| Article Data: | 127 |
| Molecular Structure: | |
|
|
|
| Formula: | C14H8O4 |
| Molecular Weight: | 240.215 |
| Synonyms: | Alizarin B(6CI);Anthraquinone, 1,2-dihydroxy- (8CI);1,2-Anthraquinonediol;1,2-Dihydroxy-9,10-anthracenedione;Acid Metachrome Red B;Acid Mordant Red B;Alizarin;Alizarin Red;Alizarina;Alizarine;Alizarine 3B;Alizarine B;Alizarine Indicator;Alizarine L Paste;Alizarine Lake Red 2P;Alizarine LakeRed 3P;Alizarine NAC;Alizarine Paste 20 percentBluish;Alizarine Red B;Alizarine Red B2;Alizarine Red L;C Ext. Red 62;C.I. 58000;C.I. Mordant Red11;D And C Orange Number 15;Mitsui Alizarine B;NSC 7212;Qiansu;Turkey red; |
| EINECS: | 200-782-5 |
| Density: | 1.54 g/cm3 |
| Melting Point: | 287 °C |
| Boiling Point: | 430 °C at 760 mmHg |
| Flash Point: | 228 °C |
| Solubility: | Soluble in hexane and chloroform. Slightly soluble in water. |
| Appearance: | orange-red crystals or powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/38-36/37/38 |
| Safety: | 26-36-24/25-22 |
| PSA: | 74.60000 |
| LogP: | 1.87320 |
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| Conditions | Yield |
|---|---|
| With aluminium trichloride In nitrobenzene at 80℃; for 0.25h; | 60% |
| With aluminium trichloride; C6H4NO2 at 165℃; for 4h; Fridel-Crafts acylation; |
| Conditions | Yield |
|---|---|
| With aluminium trichloride; sodium chloride at 165℃; for 4h; Fridel-Crafts acylation; | 55% |
| Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel Crafts Acylation; Stage #2: With hydrogenchloride In water at 0 - 100℃; for 0.75h; Heating / reflux; | 55% |
| Stage #1: phthalic anhydride; benzene-1,2-diol With aluminum (III) chloride; sodium chloride at 110 - 165℃; for 4h; Friedel-Crafts Acylation; Stage #2: With hydrogenchloride In water at 20 - 100℃; for 0.75h; | 36% |
- 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 | Yield |
|---|---|
| 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% |
- 117-79-3
2-aminoanthraquinone
A
- 72-48-0
1,2-dihydroxy-9,10-anthracenedione
B
- 81-77-6
6,15-dihydroanthrazine-5,9,14,18-tetrone
C
- 16135-99-2
16-hydroxy-8,17-dihydrodinaphtho<2,3-a:2',3'-i>phenazine-5,10,15,18-tetrone
| Conditions | Yield |
|---|---|
| With potassium hydroxide; potassium chlorate In various solvent(s) at 168 - 172℃; for 2h; | A n/a B 48% C n/a |
| With potassium hydroxide; potassium chlorate In 2-ethoxy-ethanol at 168 - 172℃; for 2h; Product distribution; further solvents and oxidants; |
| Conditions | Yield |
|---|---|
| beim Schmelzen; |
- 85-44-9
phthalic anhydride
- 493-09-4
benzo-1,4-dioxane
A
- 483-35-2
hystazarin
B
- 72-48-0
1,2-dihydroxy-9,10-anthracenedione
| Conditions | Yield |
|---|---|
| With aluminium trichloride; sodium chloride at 130 - 140℃; | |
| With aluminium trichloride; sodium chloride at 170 - 180℃; |
| Conditions | Yield |
|---|---|
| With aluminium trichloride; sodium chloride at 130 - 140℃; | |
| With aluminium trichloride; sodium chloride at 170 - 180℃; |
| Conditions | Yield |
|---|---|
| With sulfuric acid; boric acid at 240 - 255℃; |
- 85-44-9
phthalic anhydride
- 120-80-9
benzene-1,2-diol
A
- 483-35-2
hystazarin
B
- 72-48-0
1,2-dihydroxy-9,10-anthracenedione
| Conditions | Yield |
|---|---|
| With Japanese acid earth | |
| With sulfuric acid at 180 - 200℃; | |
| With aluminium trichloride; sulfuric acid; sodium chloride 1.) reflux, 2 h, 2.) reflux, 3 h; Multistep reaction. Title compound not separated from byproducts; |
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Chemistry
.
Empirical Formula: C14H8O4
Molecular Weight: 240.2109
EINECS: 200-782-5
Index of Refraction: 1.732
Molar Refractivity: 62.43 cm3
Molar Volume: 155.9 cm3
Surface Tension: 79.2 dyne/cm
Density: 1.54 g/cm3
Flash Point: 228 °C
Enthalpy of Vaporization: 71.19 kJ/mol
Boiling Point: 430 °C at 760 mmHg
Vapour Pressure: 5.34E-08 mmHg at 25 °C
Melting point: 287 °C
Appearance: Orange-red crystals or powder
Structure of 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0):
IUPAC Name: 1,2-Dihydroxyanthracene-9,10-dione
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3)O)O
InChI: InChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
InChIKey: RGCKGOZRHPZPFP-UHFFFAOYSA-N
Product Category of 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0): Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Hydroxyanthraquinones
Uses
1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0) can be used as dye intermediates and acid-base indicator.
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.: 1972,101. | ||
| 2. | mmo-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
| 3. | mma-sat 100 µg/plate | MUREAV Mutation Research. 40 (1976),203. | ||
| 4. | dnr-bcs 2 mg/disc | TRENAF Kenkyu Nenpo-Tokyo-toritsu Eisei Kenkyusho. Annual Report of Tokyo Metropolitan Research Laboratory of Public Health. 27 (1976),153. | ||
| 5. | orl-bwd LD50:316 mg/kg | AECTCV Archives of Environmental Contamination and Toxicology. 12 (1983),355. |
Consensus Reports
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Safety Profile
Poison by ingestion. Mutation data reported. An eye irritant. Flammable when exposed to oxidizers and heat. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard symbols: 
Xi.
Risk statements: 36/38-36/37/38.
36/38: Irritating to eyes and skin.
36/37/38: Irritating to eyes, respiratory system and skin.
Safety statements: 26-36-24/25-22.
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
36: Wear suitable protective clothing.
22: Do not breathe dust.
24/25: Avoid contact with skin and eyes.
Specification
1,2-Dihydroxy-9,10-anthracenedione , its cas register number is 72-48-0. It also can be called C.I. 58000 ; Mordant Red 11 ; 1,2-Dihydroxyanthraquinone ; Alizarin Red ; Dihydroxy-9,10-anthracenedione ; and 1,2-Dihydroxy anthraquinone . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, 1,2-Dihydroxy-9,10-anthracenedione (CAS NO.72-48-0) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.