81-55-0

Basic information

• Product Name: 1,8-Dihydroxy-4,5-dinitroanthraquinone
• Synonyms: 4,5 DINITROCHRYSAZINE;1,8-DINITRO-4,5-DIHYDROXYANTHRAQUINONE;1,8-DIHYDROXY-4,5-DINITRO-9,10-ANTHRAQUINONE;1,8-DIHYDROXY-4,5-DINITROANTHRACENE-9,10-DIONE;1,8-DIHYDROXY-4,5-DINITROANTHRAQUINONE;1,8 DIHYDROXY 4,5 DINITRO AQ;TIMTEC-BB SBB006491;1,8-dihydroxy-4,5-dinitro-10-anthracenedione
• CAS NO: 81-55-0
• Molecular Formula: C₁₄H₆N₂O₈
• Molecular Weight: 330.21
• EINECS: 201-360-3
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Anthraquinones;Hydroxyanthraquinones;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 81-55-0.mol

Chemical Properties

• Melting Point: 225 °C (dec.)(lit.)
• Boiling Point: 467.67°C (rough estimate)
• Flash Point: 280.9 °C
• Appearance: brownish-gold solid
• Density: 1.4944 (rough estimate)
• Vapor Pressure: 1.57E-18mmHg at 25°C
• Refractive Index: 1.5910 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane (Very Slightly, Heated, Sonicated), DMSO (Slightly)
• PKA: 3.45±0.20(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 1,8-Dihydroxy-4,5-dinitroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Dihydroxy-4,5-dinitroanthraquinone(81-55-0)
• EPA Substance Registry System: 1,8-Dihydroxy-4,5-dinitroanthraquinone(81-55-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CB6700000
• TSCA: Yes
• Hazardous Substances Data: 81-55-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,8-Dihydroxy-4,5-dinitroanthraquinone is used as a NS2B-NS3 protease specific inhibitor for the treatment of Dengue and West Nile virus infections. Its unique molecular structure allows it to target and inhibit the activity of the NS2B-NS3 protease, which is essential for the replication and maturation of these viruses. By inhibiting this protease, 1,8-Dihydroxy-4,5-dinitroanthraquinone can effectively reduce viral replication and alleviate the symptoms associated with Dengue and West Nile virus infections. This makes it a promising therapeutic agent for the treatment of these viral diseases.

Air & Water Reactions

The neat (pure) material is sensitive to air and may be sensitive to light. . Insoluble in water.

Reactivity Profile

A nitrated alcohol and a ketone. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

Flash point data for 1,8-Dihydroxy-4,5-dinitroanthraquinone are not available, however, 1,8-Dihydroxy-4,5-dinitroanthraquinone is probably combustible.

InChI:InChI=1/C14H6N2O8/c17-7-3-1-5(15(21)22)9-11(7)14(20)12-8(18)4-2-6(16(23)24)10(12)13(9)19/h1-4,17-18H

Upstream product

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

Downstream Products

• 128-94-9 1,8-diamino-4,5-dihydroxyanthraquinone 
• 17418-72-3 4,5-diamino-1,8-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2,7-disulfonic acid 
• 81-60-7 1,4,5,8-tetrahydroxy-anthraquinone 
• 24069-55-4 1,8-dihydroxy-4-amino-5-nitro-anthraquinone 
• 2177-10-8 1-amino-5-nitro-4,8-dihydroxyanthraquinone 
• 16058-60-9 C₂₀H₁₁ClN₂O₆ 
• 1010440-97-7 C₂₀H₁₀BrClN₂O₆ 
• 1010440-96-6 C₂₀H₁₀BrClN₂O₆ 
• 1010440-98-8 C₂₀H₉Br₂ClN₂O₆ 
• 65235-71-4 2-Bromo-1,8-dihydroxy-4,5-dinitro-anthraquinone 
• 65235-72-5 2,7-Dibromo-1,8-dihydroxy-4,5-dinitro-anthraquinone 
• 1310827-70-3 1,8-dihydroxy-4-(4-hydroxyphenylamino)-5-nitroanthracene-9,10-dione 
• 1310827-71-4 4-(4,5-dihydroxy-8-nitro-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)phenyl methacrylate 

Relevant articles and documents

An improved practical synthesis of leuco-1,4,5,8-tetrahydroxyanthraquinone

Leuco-1,4,5,8-tetrahydroxyanthraquinone was prepared from chrysazin by nitration and reduction with iron powder, followed by treatment with sodium hydrosulfite in alkaline solution. This method is suitable for scaling, and is significant and improved over literature methods.

An improved procedure for the preparation of 4,5-dinitrochrysazin

Pure 4,5-dinitrochrysazin was prepared by selective nitration of chrysazin, followed by solvent extraction of impurities. This method is suitable for scaling without need of chromatography, and represents a significant improvement over literature methods.