1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione

Base Information

• Chemical Name: 1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione
• CAS No.: 15939-83-0
• Molecular Formula: C26H18N2O4
• Molecular Weight: 422.44
• DSSTox Substance ID: DTXSID60594238
• Wikidata: Q82489023
• Mol file: 15939-83-0.mol

Synonyms:15939-83-0;1,4-Bis((4-hydroxyphenyl)amino)anthracene-9,10-dione;SCHEMBL5271808;DTXSID60594238;1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione

Chemical Property of 1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione

Chemical Property:

• XLogP3: 6.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 422.12665706
• Heavy Atom Count: 32
• Complexity: 625

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)NC4=CC=C(C=C4)O)NC5=CC=C(C=C5)O

Technology Process of 1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione

There total 4 articles about 1,4-Bis(4-hydroxyanilino)anthracene-9,10-dione 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-dichloroanthraquinone (602-25-5) + 4-amino-phenol (123-30-8) → 1,4-bis(4-hydroxyphenylamino)anthraquinone (15939-83-0)

Guidance literature:

With disodium hydrogenphosphate; In 1-methyl-pyrrolidin-2-one; at 150 - 180 ℃; for 15h; Inert atmosphere;

DOI:10.3762/bjoc.9.48

Reference yield:

2,5-dichlorobenzoyl chloride (2905-61-5) → 1,4-bis(4-hydroxyphenylamino)anthraquinone (15939-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 4 h / 150 °C

2: disodium hydrogenphosphate / 1-methyl-pyrrolidin-2-one / 15 h / 150 - 180 °C / Inert atmosphere

With disodium hydrogenphosphate; sulfuric acid; In 1-methyl-pyrrolidin-2-one;

DOI:10.3762/bjoc.9.48

Reference yield:

para-dichlorobenzene (106-46-7,84348-21-0) → 1,4-bis(4-hydroxyphenylamino)anthraquinone (15939-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1: phthalic anhydride; aluminum (III) chloride; sodium chloride / 6 h / 115 °C

2: sulfuric acid / 4 h / 150 °C

3: disodium hydrogenphosphate / 1-methyl-pyrrolidin-2-one / 15 h / 150 - 180 °C / Inert atmosphere

With aluminum (III) chloride; disodium hydrogenphosphate; phthalic anhydride; sulfuric acid; sodium chloride; In 1-methyl-pyrrolidin-2-one; 1: |Friedel-Crafts Acylation;

DOI:10.3762/bjoc.9.48

upstream raw materials:

1,4-dichloroanthraquinone

4-amino-phenol

2,5-dichlorobenzoyl chloride

para-dichlorobenzene

Downstream raw materials:

1,4-bis(4-((2-hydroxyethyl)oxy)phenylamino)anthraquinone

1,4-bis(4-((2-methacryloxyethyl)oxy)phenylamino)anthraquinone