131401-54-2

Basic information

• Product Name: 1,4-Difluoro-5,8-dihydroxyanthraquinone
• Synonyms: 1,4-Difluoro-5,8-dihydroxyanthraquinone;1,4-Difluoro-5,8-dihydroxy-9,10-anthracenedione;1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione
• CAS NO: 131401-54-2
• Molecular Formula: C₁₄H₆F₂O₄
• Molecular Weight: 276.1918464
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 131401-54-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 502.841°C at 760 mmHg
• Flash Point: 257.909°C
• Appearance: /
• Density: 1.681g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.684
• Solubility: Chloroform
• CAS DataBase Reference: 1,4-Difluoro-5,8-dihydroxyanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Difluoro-5,8-dihydroxyanthraquinone(131401-54-2)
• EPA Substance Registry System: 1,4-Difluoro-5,8-dihydroxyanthraquinone(131401-54-2)

Safety Data

• Hazardous Substances Data: 131401-54-2(Hazardous Substances Data)

Usage

Description

1,4-Difluoro-5,8-dihydroxyanthraquinone is an organic compound characterized by its dark purple solid appearance. It is an intermediate in the synthesis of various therapeutic anthraquinones, which are known for their medicinal properties.

Uses

Used in Pharmaceutical Industry:
1,4-Difluoro-5,8-dihydroxyanthraquinone is used as an intermediate for the production of many therapeutic anthraquinones. Its role in the pharmaceutical industry is crucial, as these anthraquinones have a wide range of applications in medicine, including the treatment of various diseases and conditions.
Used in Chemical Synthesis:
As a dark purple solid, 1,4-Difluoro-5,8-dihydroxyanthraquinone is also utilized in chemical synthesis processes. Its unique chemical properties make it a valuable component in the creation of other compounds and materials with specific characteristics and applications.

InChI:InChI=1/C14H6F2O4/c15-5-1-2-6(16)10-9(5)13(19)11-7(17)3-4-8(18)12(11)14(10)20/h1-4,17-18H

Upstream product

• 4466-59-5 3,6-dichlorophthalic anhydride 
• 123-31-9 hydroquinone 
• 652-40-4 3,6-difluorophthalic anhydride 
• 131401-58-6 3,6-difluoro-2-(2',5'-dimethoxybenzyl)benzoic acid 
• 131401-59-7 1,4-difluoro-6,9-dimethoxyanthracene-10-one 
• 131401-56-4 2-<(diethylamino)carbonyl>-3,6-difluorobenzoic acid 
• 131401-55-3 2,5-difluoro-N,N-diethylbenzamide 
• 35730-09-7 2,5-difluorobenzoyl chloride 
• 651-97-8 3,6-difluoro phthalic acid 
• 62268-16-0 3,4,6-trichlorophthalic acid 
• 16110-99-9 3,6-dichlorophthalic acid 
• 117-08-8 tetrachlorophthalic anhydride 
• 632-58-6 tetrachlorophthalic acid 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 65271-80-9 novantrone 
• 19871-57-9 1,4-bis(3-aminopropylamino)-5,8-dihydroxyanthracene-9,10-dione 
• 1195810-93-5 1-fluoro-5,8-dihydroxy-4-((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione 
• 16517-70-7 5,8-Diamino-1,4-dihydroxy-9,10-anthracenedione 
• 134566-65-7 1-<<2-(dimethylamino)ethyl>amino>-4-<<2-<2-(hydroxyethyl)amino>ethyl>amino>-5,8-dihydroxyanthracene-9,10-dione 
• 70945-59-4 1,4-Bis(2-piperidinoaethylamino)-5,8-dihydroxyanthrachinon 
• 69895-68-7 1,4-bis {[2-(dimethylamino)ethyl]amino}anthracene-9,10-dione 
• 134529-38-7 6-Fluoro-8,11-dihydroxy-4-(2-hydroxy-ethyl)-1,2,3,4-tetrahydro-1,4-diaza-benzo[a]anthracene-7,12-dione 

Relevant articles and documents

A large-scale synthesis of the bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)

A large-scale synthesis of the bis-bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxy-anthracene-9,10-dione bis-N-oxide (AQ4N) has been developed. This six-step synthesis provides AQ4N in 20% overall yield from readily available tetrachlorophthalic anhydride. The key step was a KF-NaF-mediated conversion of 3,6-dichlorophthalic anhydride to 3,6-difluorophthalic anhydride, which could be achieved in 77% yield on a 100 g scale. A trace impurity in AQ4N was determined (by LC-MS and independent synthesis) to be the mono-N-oxide 1-amino-4-[2-(dimethylamino)ethyl]amino-5,8-dihydroxyanthracene-9,10-dione N-oxide. This is formed spontaneously from AQ4N under a number of conditions, including during HPLC on reversed-phase columns. The Royal Society of Chemistry 1999.

NEW COMPOUNDS AND USES THEREOF

The present invention provides an anthraquinone compound of formula I (such as the compounds of formulae II to X) and processes for making the same. The invention further provides pharmaceutical compositions for use in the treatment of cancer, optionally in combination with an agent capable of reducing the level of oxygenation of a tumour. Additionally the invention provides an option for combination with chemotherapeutic and radiotherapeutic modalities to enhance overall tumour cell kill. The invention additionally provides methods for the detection of cellular hypoxia, both in vivo and in vitro.

PROCESS FOR THE PREPARATION OF AQ4N

A process for the preparation of compound AQ4N of formula (2) or a salt or solvate thereof wherein the said process includes the reaction step: Formula (1), Formula (2), where compound AQ4 of formula (1) is oxidised to compound AQ4N of formula (2) with an oxidising agent at a reaction temperature not exceeding 10°C.