517-92-0

Basic information

• Product Name: 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone
• Synonyms: 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone;1,8-Dihydroxy-2,4,5,7-tetranitro-9,10-anthracenedione;1,8-Dihydroxy-2,4,5,7-tetranitro-9,10-anthraquinone;2,4,5,7-Tetranitrochrysazin
• CAS NO: 517-92-0
• Molecular Formula: C₁₄H₄N₄O₁₂
• Molecular Weight: 420.20116
• EINECS: 208-246-2
• Mol File: 517-92-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: >200 °C (decomp)
• Boiling Point: 537.46°C (rough estimate)
• Flash Point: 286.3°C
• Appearance: /
• Density: 1.6285 (rough estimate)
• Vapor Pressure: 2.85E-20mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: 0.07±0.20(Predicted)
• CAS DataBase Reference: 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone(517-92-0)
• EPA Substance Registry System: 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone(517-92-0)

Safety Data

• Hazardous Substances Data: 517-92-0(Hazardous Substances Data)

Usage

General Description

1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone is a chemical compound that belongs to the family of anthraquinones, which are aromatic organic compounds. It is a yellow-to-orange crystalline powder that is primarily used as a high-energy oxidizer and component in solid rocket propellants. It is also employed as a red dye and as a precursor for the synthesis of other organic compounds. Due to its explosive nature and potential for toxicity, the handling and storage of 1,8-dihydroxy-2,4,5,7-tetranitroanthraquinone should be carried out with extreme care and in compliance with safety regulations.

InChI:InChI=1/C14H4N4O12/c19-11-5(17(27)28)1-3(15(23)24)7-9(11)14(22)10-8(13(7)21)4(16(25)26)2-6(12(10)20)18(29)30/h1-2,19-20H

Upstream product

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

Downstream Products

• 33927-45-6 3-hydroxy-2,4,6-trinitro-benzoic acid 
• 88-89-1 2,4,6-Trinitrophenol 

Relevant articles and documents

Synthesis and biological evaluation of new derivatives of emodin

Synthesis and characterization of new emodin derivatives. Cytostatic potential and binding to multi-drug-resistance transporters were evaluated. Drugs containing an anthraquinone moiety such as daunorubicin (Daunoblastin) and mitoxantrone (Onkotrone) constitute some of the most powerful cytostatics. They suppress tumor growth mainly by intercalation into DNA and inhibition of topoisomerase II, and are suspected to generate free radicals leading to DNA strand scission. We established a novel strategy for obtaining new highly functionalized derivatives of emodin (1,3,8-trihydroxy-6- methyl-anthraquinone). Using emodin, DIB, and an appropriate amine as starting materials, we obtained a wide range of emodin-related structures by one-pot synthesis. Several of these derivatives showed stronger cytotoxic and cytostatic activity than emodin. In particular, compound 6 was highly effective on the HepG2 tumor cell line, but did not show any cytotoxicity on normal hepatocytes. In addition to this favorable feature, compound 6 revealed interesting binding properties to a recombinant fragment of the multi-drug-resistance transporter, pgp, and reversed the multi-drug-resistance phenotype of H4-II-E cells, thus making this compound a promising potential anti-tumor drug.