4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Base Information

• Chemical Name: 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
• CAS No.: 25186-77-0
• Molecular Formula: C15H8 O5
• Molecular Weight: 268.226
• Mol file: 25186-77-0.mol

Synonyms:2-Anthraquinonecarboxylicacid, 4-hydroxy- (6CI); 2-Anthroic acid, 9,10-dihydro-4-hydroxy-9,10-dioxo-(8CI); 1-Hydroxyanthraquinone-3-carboxylic acid;4-Hydroxy-2-carboxyanthraquinone; Pachybasic acid

Chemical Property of 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.18E-13mmHg at 25°C
• Boiling Point: 560.2°C at 760 mmHg
• Flash Point: 306.7°C
• PSA: 91.67000
• Density: 1.577g/cm³
• LogP: 1.86580

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

There total 13 articles about 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 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: 94.0%

Ethyl 9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenecarboxylate (152039-19-5) → 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (25186-77-0)

Guidance literature:

With water; sodium hydroxide; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2016.11.029

Reference yield:

2-chloro-1,4-dimethoxybenzene (2100-42-7) → 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (25186-77-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / hexamethylenetetramine / 12 h / Heating

2: 65 percent / NaH / EtOH / toluene / 1 h / Ambient temperature

3: 70 percent / NaOAc / 3 h / 140 °C

4: 75 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1 h / 25 °C

5: 85 percent / ethanol / 5 h / Heating

6: 85 percent / 10percent aq. NaOH / 24 h / Ambient temperature

With sodium hydroxide; ammonium cerium(IV) nitrate; hexamethylenetetramine; sodium acetate; sodium hydride; EtOH; In ethanol; water; toluene; acetonitrile;

DOI:10.1021/jo00079a042

Reference yield:

4-chloro-2,5-dimethoxybenzaldehyde (90064-48-5) → 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (25186-77-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / NaH / EtOH / toluene / 1 h / Ambient temperature

2: 70 percent / NaOAc / 3 h / 140 °C

3: 75 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1 h / 25 °C

4: 85 percent / ethanol / 5 h / Heating

5: 85 percent / 10percent aq. NaOH / 24 h / Ambient temperature

With sodium hydroxide; ammonium cerium(IV) nitrate; sodium acetate; sodium hydride; EtOH; In ethanol; water; toluene; acetonitrile;

DOI:10.1021/jo00079a042

upstream raw materials:

1-acetoxy-3-methyl-anthraquinone

3'-methoxy-2,4'-carbonyl-di-benzoic acid

Ethyl 9,10-dihydro-4-hydroxy-9,10-dioxo-2-anthracenecarboxylate

sulfuric acid

Downstream raw materials:

1-hydroxyanthraquinone