1,5-DIHYDROXYANTHRAQUINONE Chemical Properties

Melting point:

279 °C (dec.)(lit.)

Boiling point:

342.92°C (rough estimate)

Density 

1.56 g/cm³

vapor density 

8.3 (vs air)

refractive index 

1.5430 (estimate)

storage temp. 

-20°C Freezer

solubility 

Poor solubility in all solvents tested.DMSO (Sparingly)

form 

Solid

pka

6.42±0.20(Predicted)

color 

Yellow to Green

Merck 

14,689

BRN 

1881718

CAS DataBase Reference

117-12-4(CAS DataBase Reference)

EPA Substance Registry System

Anthrarufin (117-12-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36/37

WGK Germany 

3

RTECS 

CB6630000

TSCA 

Yes

HS Code 

29146990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,5-DIHYDROXYANTHRAQUINONE Usage And Synthesis

Chemical Properties

Yellow to Green Solid

Uses

1,5-Dihydroxyanthraquinone (anthrarufin) is an important intermediate for manufacturing disperse blue dyes. It is the key intermediates for manufacturing disperse blue dyes via dinitrodihydroxyanthraquinone and vat dyes via diaminoanthraquinones.

Uses

1,5-Dihydroxyanthraquinone is an anthraquinone derivative with suppressive effects against nitric oxide (NO) synthase. Potential antimalarial agent. Used in studies as a potential competitive non-peptidic inhibitor of HIV-1 protei nase.

Uses

Important intermediate in the manufacture of alizarin and indanthrene dyestuffs. Forms insoluble Ba and Ca lakes; has been proposed as analytical reagent for the detection of Ca.

Definition

ChEBI: A dihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1 and 5.

Synthesis

1,5-Dihydroxyanthraquinone is prepared from 1,5-anthraquinonedisulfonic acid by replacing the SO3H groups, and from 1,5-dinitroanthraquinone by directly replacing the nitro groups, e.g., in sulfolane with calcium oxide or, more effectively, via 1,5- dimethoxyanthraquinone and subsequent hydrolysis of the ether linkage.

Purification Methods

Purify anthrarufin by column chromatography on silica gel with CHCl3/Et2O as eluent, followed by recrystallisation from acetone. Alternatively recrystallise it from glacial acetic acid [Flom & Barbara J Phys Chem 89 4489 1985]. [Beilstein 7 III 2359, 8 IV 3268.]

1,5-DIHYDROXYANTHRAQUINONE(117-12-4)Related Product Information

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