1-Chloro-4-hydroxyanthraquinone

Base Information

• Chemical Name: 1-Chloro-4-hydroxyanthraquinone
• CAS No.: 82-42-8
• Molecular Formula: C14H7ClO3
• Molecular Weight: 258.661
• European Community (EC) Number: 201-419-3
• NSC Number: 508993
• UNII: 50T4JF2H1K
• DSSTox Substance ID: DTXSID3058872
• Nikkaji Number: J192.602K
• Wikidata: Q27260818
• Mol file: 82-42-8.mol

Synonyms:1-Chloro-4-hydroxyanthraquinone;82-42-8;1-chloro-4-hydroxyanthracene-9,10-dione;9,10-Anthracenedione, 1-chloro-4-hydroxy-;1-Hydroxy-4-chloroanthraquinone;Anthraquinone, 1-chloro-4-hydroxy-;C14H7ClO3;UNII-50T4JF2H1K;50T4JF2H1K;EINECS 201-419-3;NSC 508993;NSC-508993;NSC508993;1-Chlor-4-oxyanthrachinon;9, 1-chloro-4-hydroxy-;1-chlor-4-hydroxyanthraquinon;SCHEMBL6905105;C14-H7-Cl-O3;DTXSID3058872;TUZZWPYZPHNFJY-UHFFFAOYSA-;1-chloro-4-hydroxy anthraquinone;AKOS022507335;1-Hydroxy-4-chloro-9,10-anthraquinone;1-chloro-4-hydroxy-anthracene-9,10-dione;1-Chloro-4-hydroxyanthra-9,10-quinone #;1-CHLORO-4-HYDROXY-9,10-ANTHRAQUINONE;Q27260818

Chemical Property of 1-Chloro-4-hydroxyanthraquinone

Chemical Property:

• Vapor Pressure: 2.17E-09mmHg at 25°C
• Refractive Index: 1.699
• Boiling Point: 468.3 °C at 760 mmHg
• Flash Point: 237 °C
• PSA: 54.37000
• Density: 1.526 g/cm³
• LogP: 2.82100
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 258.0083718
• Heavy Atom Count: 18
• Complexity: 381

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)Cl)O

Technology Process of 1-Chloro-4-hydroxyanthraquinone

There total 23 articles about 1-Chloro-4-hydroxyanthraquinone 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%

phthalic anhydride (85-44-9) + 4-chloro-phenol (106-48-9,82344-39-6) → 4-chloro-1-hydroxyanthraquinone (82-42-8)

Guidance literature:

phthalic anhydride; 4-chloro-phenol; With aluminum (III) chloride; at 150 - 160 ℃; for 0.5h;

With sulfuric acid; at 95 ℃; for 1h;

DOI:10.2174/157018011796235185

Reference yield: 91.0%

1-fluoroanthracene-9,10-dione derivative (2994-43-6) → 4-chloro-1-hydroxyanthraquinone (82-42-8)

Guidance literature:

With sodium trimethylsilanolate; In tetrahydrofuran; stirring f the mixture at room temperature under a nitrogen atmosphere for 18 h;

DOI:10.1080/00397919808004449

Reference yield: 61.8%

1,4-dichloroanthraquinone (602-25-5) → 4-chloro-1-hydroxyanthraquinone (82-42-8)

Guidance literature:

With sulfuric acid; for 100h; Product distribution; Irradiation; further 1-chloroanthraquinones;

DOI:10.1246/cl.1980.1493

upstream raw materials:

phthalic anhydride

4-chloro-phenol

1-hydroxyanthraquinone

2-(5'-chloro-2'-hydroxybenzoyl)benzoic acid

Downstream raw materials:

1,4-dihydroxy-9,10-anthracenedione

1-amino-3-bromo-4-hydroxyanthraquinone

N-(3-bromo-4-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthryl)-toluene-4-sulfonamide

1-benzoyloxy-4-chloro-9,10-anthraquinone

Refernces

• 1、 Saha, Koushik,Lajis, Nordin H.,Abas, Faridah,Naji, Nabil Ali,Hamzah, A. Sazali,Shaari, Khozirah. "Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation". . p. 821 - 825. Retrieved 2008/12/22.
• 2、 Krapcho, A. Paul,Waterhouse, David. "Sodium trimethyl silanoate. A hydroxyl synthon for fluoride S(n)Ar type displacements from anthracene-9,10-diones, benz[g]isoquinoline-5-10-diones and nitrobenzenes". . p. 3415 - 3422. Retrieved 2007/10/03.