1,6-DIHYDROXY-ANTHRAQUINONE

Base Information

• Chemical Name: 1,6-DIHYDROXY-ANTHRAQUINONE
• CAS No.: 569-10-8
• Molecular Formula: C14H8O4
• Molecular Weight: 240.21100
• Mol file: 569-10-8.mol

Synonyms:1,6-Dihydroxy-9,10-anthraquinone;1,6-dihydroxy-9,10-anthracenedione;1,6-Dihydroxy-anthrachinon;3,8-dihydroxy anthraquinone;9,10-Anthracenedione, 1,6-dihydroxy-;

Chemical Property of 1,6-DIHYDROXY-ANTHRAQUINONE

Chemical Property:

• PSA: 74.60000
• LogP: 1.87320

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,6-DIHYDROXY-ANTHRAQUINONE

There total 22 articles about 1,6-DIHYDROXY-ANTHRAQUINONE 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: 85.0%

2-(4-methoxybenzoyl)-3-methoxybenzoic acid (80764-47-2) → 1,6-dihydroxy-9,10-anthraquinone (569-10-8)

Guidance literature:

at 155 - 160 ℃; for 14h; Inert atmosphere;

DOI:10.1002/ejoc.200900960

Reference yield:

danishefsky's diene (54125-02-9) + 2-acetoxy-3-chloro-5-methoxy-1,4-naphthoquinone (275799-12-7) → 1,6-dihydroxy-9,10-anthraquinone (569-10-8) + 1,7-dihydroxy-anthraquinone (569-08-4)

Guidance literature:

danishefsky's diene; 2-acetoxy-3-chloro-5-methoxy-1,4-naphthoquinone; In benzene; at 50 ℃; for 72h;

With acetic acid; zinc; at 20 ℃;

With aluminium trichloride; sodium chloride; at 140 ℃;

DOI:10.1071/CH99179

Reference yield:

2-acetoxy-3-chloro-5-hydroxy-1,4-naphthoquinone → 1,6-dihydroxy-9,10-anthraquinone (569-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 96 h / 20 °C

2: 37 mg / Zn; glac. HOAc / 20 °C

With acetic acid; zinc; In benzene; 1: Diels-Alder cycloaddition / 2: Reduction;

DOI:10.1071/CH99179

upstream raw materials:

1,6-Dimethoxy-9,10-anthracenedione

3-hydroxy-2-(4-methoxy-benzoyl)-benzoic acid

1,6-Diamino-9,10-anthraquinone

5-hydroxynaphtho-1,4-quinone

Downstream raw materials:

2,3,6-trihydroxyacetophenone

Refernces

• 1、 Cameron, Donald W.. "Reaction of 2-acetoxy-3-chloro and 2,3-diacetoxy naphthoquinones with 1,3-dioxy and 1,1,3-trioxy butadienes". . p. 1165 - 1171. Retrieved 2007/10/03.
• 2、 Camerom, Donald W.,Feutrill, Geoffrey I.,Keep, Philip L. C.. "DICHLORO QUINONES AS DIENOPHILES; SYNTHESIS OF ALIZARIN DERIVATIVES". . p. 5173 - 5176. Retrieved 2007/10/02.