Anthracene-1,4,9,10-tetraol

Base Information

• Chemical Name: Anthracene-1,4,9,10-tetraol
• CAS No.: 476-60-8
• Molecular Formula: C14H10 O4
• Molecular Weight: 242.231
• European Community (EC) Number: 207-507-8
• NSC Number: 15369
• UNII: CP3E23813Z
• DSSTox Substance ID: DTXSID1060057
• Nikkaji Number: J824I
• Wikidata: Q27275591
• ChEMBL ID: CHEMBL4853146
• Mol file: 476-60-8.mol

Synonyms:1,4,9,10-tetrahydroxyanthracene;leucoquinizarin

Chemical Property of Anthracene-1,4,9,10-tetraol

Chemical Property:

• Appearance/Colour: Light yellow powder.
• Vapor Pressure: 4.74E-17mmHg at 25°C
• Melting Point: 151 ºC
• Refractive Index: 1.5190 (estimate)
• Boiling Point: 641.4 °C at 760 mmHg
• PKA: 8.11±0.30(Predicted)
• Flash Point: 322.7 °C
• PSA: 80.92000
• Density: 1.6 g/cm³
• LogP: 2.81540
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 242.05790880
• Heavy Atom Count: 18
• Complexity: 278

Purity/Quality:

99% ^*data from raw suppliers

Leucoquinizarin >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C3C(=CC=C(C3=C2O)O)O)O

Technology Process of Anthracene-1,4,9,10-tetraol

There total 4 articles about Anthracene-1,4,9,10-tetraol 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: 92.7%

1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) → leucoquinizarin (476-60-8)

Guidance literature:

1,4-dihydroxy-9,10-anthracenedione; With boric acid; In methanol; at 20 ℃; for 0.0833333h; Autoclave;

With hydrogen; In methanol; at 65 ℃; for 6h; under 3375.34 - 5925.59 Torr; Pressure; Temperature; Autoclave;

Reference yield:

1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8) → leucoquinizarin (476-60-8) + 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2,79248-79-6)

Guidance literature:

With ethanol; for 2.5h; Title compound not separated from byproducts; Irradiation;

DOI:10.1007/BF00659394

Reference yield:

semiquinone of 1,4-dihydroxy-anthracene-9,10-dione (59637-76-2) → leucoquinizarin (476-60-8) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1,103220-12-8)

Guidance literature:

With water; at 25 - 50 ℃; Thermodynamic data; disproportionation constant and ΔH^o and ΔS^o;

DOI:10.1039/FT9969204965

upstream raw materials:

1,4-dihydroxy-9,10-anthracenedione

semiquinone of 1,4-dihydroxy-anthracene-9,10-dione

Downstream raw materials:

6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacene-quinone

(5R)-3-O-Benzyl-1,2-O-isopropylidene-3-C-methyl-5-(9',10'-dihydro-1',4'-dihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose

(5S)-3-O-Benzyl-1,2-O-isopropylidene-3-C-methyl-5-(9',10'-dihydro-1',4'-dihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose

2-((S)-2-Benzyloxy-4,5-dihydroxy-2-methyl-pentyl)-1,4-dihydroxy-anthraquinone

Refernces

• 1、 -. "Preparation process for dihydroxyl anthraquinone leuco body". Paragraph 0015-0020. . Retrieved 2018/09/13.
• 2、 Alegria, Antonio E.,Lopez, Marcos,Guevara, Norberto. "Thermodynamics of semiquinone disproportionation in aqueous buffer". . p. 4965 - 4968. Retrieved 2007/10/03.