Danthron

Base Information

• Chemical Name: Danthron
• CAS No.: 117-10-2
• Deprecated CAS: 32073-07-7,343235-40-5,343235-40-5
• Molecular Formula: C14H8O4
• Molecular Weight: 240.215
• Hs Code.: 2914.69
• European Community (EC) Number: 204-173-5
• NSC Number: 755828,646568,38626,7210
• UN Number: 2811
• UNII: Z4XE6IBF3V
• DSSTox Substance ID: DTXSID9020328
• Nikkaji Number: J2.905J
• Wikipedia: Dantron
• Wikidata: Q5221244
• NCI Thesaurus Code: C44363
• Metabolomics Workbench ID: 44040
• ChEMBL ID: CHEMBL53418
• Mol file: 117-10-2.mol

Synonyms:1,8-dihydroxy-9,10-anthraquinone;1,8-dihydroxyanthraquinone;chrysazin;Danthane;danthron;danthrone;Dorbanex;Duolax

Chemical Property of Danthron

Chemical Property:

• Appearance/Colour: orange-brown or brown powder
• Vapor Pressure: 8.21E-09mmHg at 25°C
• Melting Point: 191-193 °C
• Refractive Index: 1.732
• Boiling Point: 452.667 °C at 760 mmHg
• PKA: 6.27±0.20(Predicted)
• Flash Point: 241.691 °C
• PSA: 74.60000
• Density: 1.541 g/cm³
• LogP: 1.87320
• Storage Temp.: Refrigerator
• Solubility.: very faint turbidity in hot Acetic acid
• Water Solubility.: insoluble
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 240.04225873
• Heavy Atom Count: 18
• Complexity: 346
• Transport DOT Label: Poison

Purity/Quality:

99%+ ^*data from raw suppliers

1,8-Dihydroxyanthraquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37-36-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
• Description: Danthron, a natural product, was originally extracted from the roots and rhizome of Polygonaceae plant, also called Da Huang in traditional Chinese herbal medicine. Now it is synthesized in many countries, such as Germany, India, Japan, Poland, the United Kingdom, and the United States. Danthron is reasonably anticipated to be a human carcinogen. Danthron is an anthraquinone that exists at room temperature as a red or orange crystalline powder.It is practically insoluble in water, but soluble in a variety of solvents (acetone, chloroform, diethyl ether, ethanol) and alkaline hydroxide solutions. The stability of danthron is generally good. It is stable under room temperatures and normal pressures.
• Uses: Important intermediate in the manufacture of alizarin and indanthrene dyestuffs; forms insoluble Ca, Ba, Pb lakes. Antioxidant in synthetic lubricants; fungicide. Used as a stimulant laxative, though due to its carcinogenic properties, is not widely prescribed. cathartic 1,8-Dihydroxyanthraquinone can be used:To prepare an inclusion complex with β-cyclodextrin, applicable as a sensor in the estimation of Cu2+?ions in an aqueous solution.As a starting material in the synthesis of 1,4,5,8-tetramethoxyanthracene.As an aromatic scavenger in the modification of lignin, which acts as a corrosion inhibitor for steel.

Technology Process of Danthron

There total 79 articles about Danthron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone) (69043-83-0) → 1,5-dihydroxyanthraquinone (117-12-4) + 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Guidance literature:

With pyrrolidine; In toluene; for 1.5h; Heating;

Reference yield: 90.0%

1,8-bis(2-phenylselenoethoxy)anthracene-9,10-dione (1432067-68-9) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2) + 1-hydroxy-8-(2-phenylselenoethoxy)anthracene-9,10-dione (1432067-84-9)

Guidance literature:

With iron (III) perchlorate monohydrate; In dichloromethane; for 2h;

DOI:10.1016/j.poly.2013.03.003

Reference yield: 86.0%

4-hydroxy-10-imino-5-methoxymethoxy-10H-anthracen-9-one (577975-52-1) → 1,8-dihydroxy-9,10-anthracenedione (117-10-2)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; methanol; at 20 ℃; for 96h;

DOI:10.1021/ja035308f

upstream raw materials:

1-hydroxy-8-methoxyanthraquinone

1,2-diamino-9,10-anthraquinone

1,8-anthraquinonedisulphonic acid

1,8-dihydroxy-3-carboxy-anthraquinone

Downstream raw materials:

1,8-diacetoxy-9,10-anthraquinone

5-<3-<1-(8-hydroxy-9,10-anthraquinonyl)oxy>tetramethyleneoxyphenyl>-10,15,20-triphenylporphine

1,8-dihydroxy-4,5-dinitro-anthraquinone

1,8-Dihydroxy-2,5-dinitro-9,10-anthracenedione

Refernces

• 1、 Taskinen,Haarala,Wartiovaara,Halmekoski. "Oxidation of antipsoriatic 10-acyldithranolderivatives and dithranol to 1,8-dihydroxyanthraquinone". . p. 103 - 106. Retrieved 1988.
• 2、 Cameron, Donald W.,Feutrill, Geoffrey I.,McKay, Peter G.. "REGIOSPECIFIC SYNTHESIS OF QUINIZARIN DERIVATIVES BY CYCLOADDITION". . p. 701 - 702. Retrieved 1981.
• 3、 Pullella, Glenn A.,Wdowiak, Adam P.,Sykes, Melissa L.,Lucantoni, Leonardo,Sukhoverkov, Kirill V.,Zulfiqar, Bilal,Sobolev, Alexandre N.,West, Nicholas P.,Mylne, Joshua S.,Avery, Vicky M.,Piggott, Matthew J.. "Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone". . p. 5519 - 5523. Retrieved 2019.
• 4、 Pal, Haridas,Palit, Dipak K.,Mukherjee, Tulal,Mittal, Jai. P.. "One-electron Reactions of 1,5- and 1,8-Dihydroxy-9,10-anthraquinones. A Pulse Radiolysis Study". . p. 1109 - 1116. Retrieved 1991.
• 5、 Maekelae, Reijo,Vuolle, Mikko. "Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance of some 9,10-Anthraquinone Radicals in Solution. Part 3. - Hydroxyanthraquinones". . p. 2569 - 2573. Retrieved 1990.
• 6、 Bardagi, Javier I.,Ghosh, Indrajit,Schmalzbauer, Matthias,Ghosh, Tamal,K?nig, Burkhard. "Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides". supporting information. p. 34 - 40. Retrieved 2018/01/01.