117-12-4

Basic information

• Product Name: 1,5-DIHYDROXYANTHRAQUINONE
• Synonyms: LABOTEST-BB LT00160027;ANTHRARUFIN;1,5-DIHYDROXYANTHRAQUINONE;1,5 DIHYDROXY AQ;RARECHEM AQ BD AN24;9,10-Anthracenedione, 1,5-dihydroxy-;Anthrarufin,80%;1,5-dihydroxyanthracene-9,10-dione
• CAS NO: 117-12-4
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21
• EINECS: 204-175-6
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones;Hydroxyanthraquinones;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators
• Mol File: 117-12-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 279 °C (dec.)(lit.)
• Boiling Point: 342.92°C (rough estimate)
• Flash Point: 241.7 °C
• Appearance: /
• Density: 1.56 g/cm3
• Vapor Density: 8.3 (vs air)
• Vapor Pressure: 8.21E-09mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: Poor solubility in all solvents tested.DMSO (Sparingly)
• PKA: 6.42±0.20(Predicted)
• Merck: 14,689
• BRN: 1881718
• CAS DataBase Reference: 1,5-DIHYDROXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIHYDROXYANTHRAQUINONE(117-12-4)
• EPA Substance Registry System: 1,5-DIHYDROXYANTHRAQUINONE(117-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37
• WGK Germany: 3
• RTECS: CB6630000
• TSCA: Yes
• Hazardous Substances Data: 117-12-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to Green Solid

Uses

Different sources of media describe the Uses of 117-12-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.

Definition

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

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.]

InChI:InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H

Upstream product

• 82-35-9 1.5-dinitroanthraquinone 
• 84-65-1 9,10-phenanthrenequinone 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 99-06-9 3-Carboxyphenol 
• 120234-88-0 1-amino-4,8-dihydroxy-9,10-anthraquinone 
• 120-12-7 anthracene 
• 117-14-6 1,5-anthraquinone disulfonate 
• 98-95-3 nitrobenzene 
• 82-50-8 5-nitroanthraquinone-1-sulfonic acid 
• 7732-18-5 water 
• 2961-04-8 1,4,5-trihydroxy-9,10-anthracenedione 
• 86278-83-3 4-ethylenedioxy-(3-nitromethyl)-pentanal 
• 69043-83-0 1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone) 

Downstream Products

• 1747-93-9 1,5-diacetoxy-9,10-anthraquinone 
• 87965-34-2 1,5-Dihydroxy-4-phenylamino-9,10-anthraquinone 
• 851636-65-2 [[nitrilotris(3,5-di-tert-butyl-2-cresolato)]Ti(1,5-dihydroxyanthraquinone(-1H)) 
• 1007895-48-8 [(tin(IV)(benzyl)3)2(μ-1,5-dihydroxy-9,10-anthracenedione(-2H))] 
• 1007895-47-7 [(tin(IV)(phenyl)3)2(μ-1,5-dihydroxy-9,10-anthracenedione(-2H))] 
• 397845-44-2 1,5-bis(benzyloxy)anthracene-9,10-dione 
• 6448-90-4 1,5-dimethoxy-anthraquinone 
• 6361-12-2 1,5-dibromo-4,8-dihydroxy-anthraquinone 
• 6837-97-4 1,5-dichloro-4,8-dihydroxyanthraquinone 
• 128-91-6 1,5-dihydroxy-4,8-dinitro-anthraquinone 
• 6492-85-9 1,5-dihydroxyanthraquinone-2,6-disulfonic acid 

Related news

Surface-enhanced Raman scattering of 1,5-DIHYDROXYANTHRAQUINONE (cas 117-12-4) in silver sol08/23/2019

Surface-enhanced Raman scattering studies on 1,5-dihydroxyanthraquinone (1,5-DHAQ) were undertaken to elucidate the molecular orientation on the silver particles and the enhancement mechanism. The 1,5-DHAQ molecule is adsorbed through its coordinating sites (CO groups) and it is found to have ...detailed

A highly selective dual mode detection of Fe3 + ion sensing based on 1,5-DIHYDROXYANTHRAQUINONE (cas 117-12-4) in the presence of β-cyclodextrin08/22/2019

1,5-Dihydroxyanthraquinone (1,5-DHAQ) and in the presence of β-cyclodextrin (β-CD) has been used to find Fe3 + ion in aqueous solution by UV–visible and fluorescence spectroscopy. The chromo-fluorogenic probe undergoes absorption and emission intensity enhancement upon binding to Fe3 + ion in...detailed

Relevant articles and documents

Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids

A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones to 1-hydroxy-2-(prop-2’-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF4 (1-methylimidazolium tetrafluoroborate), in short reaction times (5–35 min). Our study showed that 1-(prop-2’-enyloxy)anthraquinone is more active than 1-(2’-chloroprop-2’-enyloxy)anthraquinone to perform this rearrangement.

Photochemistry of 1, n -Dibenzyloxy-9,10-anthraquinones

Figure presented The photochemistry of a series of 9,10-anthraquinones with multiple benzyloxy substituents was investigated. In polar solvent, the expected Blankespoor oxidative cleavage reaction is the major reaction pathway, but in most cases, several minor products were observed. In nonpolar solvents, the abundance of these minor products increases dramatically. Four types of product were observed with the favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C-O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance of considering the medium and photoredox behavior in anthraquinone photochemistry.

Pathway of anthracene modification under simulated solar radiation

Exposure of polycyclic aromatic hydrocarbons (PAHs) to sunlight results in rapid structural photomodification generally via oxidation reactions. These PAH modification products are in many cases more toxic than their parent compounds. In this study, anthracene (ANT), a rapidly photooxidized PAH, was irradiated with simulated solar radiation (SSR, 100 μmol m-2 s- 1) in aqueous solution to examine the photomodification pathway. The photoproducts formed were identified by HPLC. The ANT product profile after 9 h in SSR was very complex, with more than 20 compounds detected. The photoproducts formed were anthraquinones, benzoic acids, benzaldehydes and phenols showing the process to be oxidative in nature. Some of the anthraquinones were themselves subject to photooxidation, and were thus intermediates in the product pathway. The kinetics of ANT photooxidation revealed a pseudo first-order reaction with a half-life of 2 h under the SSR source used. The kinetics of product formation allowed deduction of a probable photomodification pathway. This study indicates that PAH photooxidation products are likely to exist as complex, dynamically changing mixtures in PAH contaminated aquatic environments.