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CAS No.: | 117-10-2 |
---|---|
Name: | 1,8-Dihydroxyanthraquinone |
Article Data: | 56 |
Molecular Structure: | |
Formula: | C14H8O4 |
Molecular Weight: | 240.215 |
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; |
EINECS: | 204-173-5 |
Density: | 1.541 g/cm3 |
Melting Point: | 191-193 °C |
Boiling Point: | 452.667 °C at 760 mmHg |
Flash Point: | 241.691 °C |
Solubility: | insoluble in water |
Appearance: | orange-brown or brown powder |
Hazard Symbols: | Xn |
Risk Codes: | 40 |
Safety: | 36/37-22 |
PSA: | 74.60000 |
LogP: | 1.87320 |
Conditions | Yield |
---|---|
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)
A
1,5-dihydroxyanthraquinone
B
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With pyrrolidine In toluene for 1.5h; Heating; | A 93% B n/a |
1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione
A
1,8-dihydroxy-9,10-anthracenedione
B
1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione
Conditions | Yield |
---|---|
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
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane; methanol at 20℃; for 96h; | 86% |
1,8-bis(prop-2-ynyloxy)anthracene-9,10-dione
A
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With iron at 160℃; for 0.0666667h; Claisen Rearrangement; Ionic liquid; | A 16% B 73% |
1-hydroxy-8-(prop-2'-ynyloxy)anthraquinone
A
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
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
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sulfuric acid | 67% |
1,1-ethylenedioxy-6-hydroxy-1,4,4α,9aα-tetrahydro-9,10-anthraquinone
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 0.333333h; | 40% |
3-Hydroxy-2-(2-hydroxybenzoyl)-benzoesaeure
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide; boric acid at 120℃; for 0.5h; | 38.4% |
With boron trioxide; sulfuric acid at 100℃; |
A
1,8-dihydroxy-9,10-anthracenedione
Conditions | Yield |
---|---|
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 26h; Inert atmosphere; | A n/a B 34% |
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The major use of 1,8-Dihydroxyanthraquinone (117-10-2) is as an intermediate in the production of alizarin and indanthrene dyestuffs.
NTP 10th Report on Carcinogens. Reported in EPA TSCA Inventory.
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 %.
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 %.
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. |