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1,8-Dihydroxyanthraquinone

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Name

1,8-Dihydroxyanthraquinone

EINECS 204-173-5
CAS No. 117-10-2 Density 1.541 g/cm3
PSA 74.60000 LogP 1.87320
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 N/A 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;

Article Data 56

1,8-Dihydroxyanthraquinone Synthetic route

1963-82-2

1,8-diacetoxy-9,10-anthraquinone

117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With water; trifluoroacetic acid at 65℃; for 1h;100%
69043-83-0

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

A

117-12-4

1,5-dihydroxyanthraquinone

B

117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With pyrrolidine In toluene for 1.5h; Heating;A 93%
B n/a
1432067-68-9

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

A

117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

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%
577975-52-1

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

117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; methanol at 20℃; for 96h;86%
1182282-39-8

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

A

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

Conditions
ConditionsYield
With iron at 160℃; for 0.0666667h; Claisen Rearrangement; Ionic liquid;A 16%
B 73%
1393091-17-2

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

A

117-10-2

1,8-dihydroxy-9,10-anthracenedione

B

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%
84399-87-1

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

117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With sulfuric acid67%
78526-20-2

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

117-10-2

1,8-dihydroxy-9,10-anthracenedione

Conditions
ConditionsYield
With acetic acid at 100℃; for 0.333333h;40%
89646-25-3

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

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

A

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

Conditions
ConditionsYield
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 26h; Inert atmosphere;A n/a
B 34%

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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