CAS No.117-10-2,1,8-Dihydroxyanthraquinone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	117-10-2
Name:	1,8-Dihydroxyanthraquinone
Article Data:	56

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

Synthetic route

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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

: 577975-52-1
4-hydroxy-10-imino-5-methoxymethoxy-10H-anthracen-9-one

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sulfuric acid	67%

: 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

Conditions	Yield
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

Conditions	Yield
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

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

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Uses

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

Consensus Reports

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

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.