9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy-

Base Information

• Chemical Name: 9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy-
• CAS No.: 16517-70-7
• Molecular Formula: C14H10 N2 O4
• Molecular Weight: 270.244
• Hs Code.: 2922509090
• UNII: 58SUQ7J26N
• DSSTox Substance ID: DTXSID6066072
• Nikkaji Number: J421.969D
• Wikidata: Q27094784
• Metabolomics Workbench ID: 148406
• ChEMBL ID: CHEMBL572879
• Mol file: 16517-70-7.mol

Synonyms:16517-70-7;1,4-Diamino-5,8-dihydroxyanthracene-9,10-dione;1,4-Diamino-5,8-dihydroxyanthraquinone;5,8-DI-AMINO-1,4-DIHYDROXY-ANTHRAQUINONE;9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy-;1,4-diamino-5,8-dihydroxy-anthraquinone;58SUQ7J26N;1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione;5,8-Diamino-1,4-dihydroxyanthraquinone;1,4-diamino-5,8-dihydroxy-9,10-dihydroanthracene-9,10-dione;1m2r;UNII-58SUQ7J26N;5,8-DIAMINOQUINIZARIN;SCHEMBL504614;CHEMBL572879;DTXSID6066072;BDBM11315;STK229002;DB03924;1,4-diamino-5,8-dihydroxyanthra-9,10-quinone;AE-848/07100018;Q27094784;MNY

Chemical Property of 9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy-

Chemical Property:

• Vapor Pressure: 9.78E-17mmHg at 25°C
• Boiling Point: 635.3°Cat760mmHg
• Flash Point: 338°C
• PSA: 126.64000
• Density: 1.683g/cm³
• LogP: 2.20000
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 270.06405680
• Heavy Atom Count: 20
• Complexity: 401

Purity/Quality:

98%Min ^*data from raw suppliers

5,8-Diamino-1,4-dihydroxyanthraquinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1N)C(=O)C3=C(C=CC(=C3C2=O)O)O)N
• Uses: 5,8-Diamino-1,4-dihydroxyanthraquinone is an inhibitor of protein kinase CK2.

Technology Process of 9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy-

There total 10 articles about 9,10-Anthracenedione, 1,4-diamino-5,8-dihydroxy- 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: 88.0%

1,4-diamino-9,10-anthraquinone (128-95-0) → 5,8-Diamino-1,4-dihydroxy-9,10-anthracenedione (16517-70-7)

Guidance literature:

With sodium chlorate; sulfuric acid; at -5 - 20 ℃; for 3h;

DOI:10.1016/j.molstruc.2016.08.007

Reference yield: 40.0%

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione (131401-54-2) → 5,8-Diamino-1,4-dihydroxy-9,10-anthracenedione (16517-70-7)

Guidance literature:

With ammonium hydroxide; In pyridine; at 110 ℃; for 3h;

DOI:10.1021/jm9013407

Reference yield:

1,4-di(benzyloxy)-5,8-dichloro-9,10-dihydro-9,10-anthracenedione (91440-79-8) → 5,8-Diamino-1,4-dihydroxy-9,10-anthracenedione (16517-70-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Cu₂I₂ / N,N-dimethyl-acetamide / 20 h / Heating

2: 0.8 g / NH₂NH₂*H₂O, K₂CO₃ / pyridine / 0.33 h / Heating

3: 250 mg / H₂, gl.AcOH / Pd(OH)2/C / 0.33 h / Ambient temperature

With copper (I) iodide; hydrogen; potassium carbonate; hydrazine hydrate; acetic acid; palladium dihydroxide; In pyridine; N,N-dimethyl acetamide;

upstream raw materials:

1,4-diamino-5,8-dimethoxy-anthraquinone

1,4-diamino-5,8-bis(phenylmethoxy)-9,10-anthracenedione

1,4-di(benzyloxy)-5,8-dichloro-9,10-dihydro-9,10-anthracenedione

1,4-diphthaliloamino-5,8-bis(phenylmethoxy)-9,10-anthracenedione

Downstream raw materials:

1,4,5,8-tetrahydroxy-anthraquinone

Refernces

• 1、 Yang, Liu,Peacey, Eleanor,Dickson, John,Donahue, Christine P.,Zheng, Suxin,Varani, Gabriele,Wolfe, Michael S.. "Mitoxantrone analogues as ligands for a stem-loop structure of tau Pre-mRNA". supporting information; experimental part. p. 6523 - 6526. Retrieved 2010/03/25.