1-Hydroxy-2-carboxyanthraquinone

Base Information

• Chemical Name: 1-Hydroxy-2-carboxyanthraquinone
• CAS No.: 7400-93-3
• Molecular Formula: C₁₅H₈O₅
• Molecular Weight: 268.226
• Mol file: 7400-93-3.mol

Synonyms:1-Hydroxy-2-carboxyanthraquinone;1-Hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure;9,10-Dihydro-1-hydroxy-9,10-dioxo-2-anthracenecarboxylic acid;1-hydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid;2-carboxy-1-hydroxyanthraquinone;1-Hydroxy-2-carboxyanthrachinon;

Chemical Property of 1-Hydroxy-2-carboxyanthraquinone

Chemical Property:

• Vapor Pressure: 1.35E-11mmHg at 25°C
• Melting Point: 224-225 °C
• Boiling Point: 519°Cat760mmHg
• PKA: 2.03±0.20(Predicted)
• Flash Point: 281.7°C
• PSA: 91.67000
• Density: 1.577g/cm³
• LogP: 1.86580

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Hydroxy-2-carboxyanthraquinone

There total 10 articles about 1-Hydroxy-2-carboxyanthraquinone 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: 12.0%

2-methyl-6,11-dihydroanthra<1,2-b>furan-6,11-dione (80034-90-8) → 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid (7400-93-3) + 2-formyl-1-hydroxyanthraquinone (56594-54-8) + 1-hydroxy-2-(1',2'-dioxopropyl)-9,10-anthraquinone + 1-hydroxy-2-(1'-hydroxy-2'-oxopropyl)-9,10-anthraquinone (110200-94-7)

Guidance literature:

With thallium(III) trifluoroacetate; In trifluoroacetic acid; for 18h;

Reference yield:

1-aminoanthraquinone-2-carboxylic acid (82-24-6) → 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid (7400-93-3)

Guidance literature:

With sulfuric acid; sodium nitrite; Multistep reaction; 1.) ice-cooling, 1 h, 2.) H₂O, 85 deg, 2 h;

DOI:10.1016/0031-9422(90)85382-P

Reference yield:

1-nitro-2-methylanthraquinone (129-15-7) → 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid (7400-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / aq. sulfuric acid, chromium trioxide / 4 h / 70 - 75 °C

2: 98 percent / aq. NaBH₄, 1percent aq. ammonia / 4 h / 25 °C

3: 1.) 90percent aq. H₂SO₄, sodium nitrite, 2.) water / 1.) from 50 to 60 deg C, 0.5 h, 2.) from 95 to 100 deg C, 2 h

With chromium(VI) oxide; ammonium hydroxide; sodium tetrahydroborate; sulfuric acid; water; sodium nitrite;

DOI:10.1021/jm00346a008

upstream raw materials:

1-methoxy-2-methyl-9,10-antraquinone

2'-hydroxy-2,4'-carbonyl-di-benzoic acid

acetic acid

1-aminoanthraquinone-2-carboxylic acid

Refernces

• 1、 Boddy, Ian K.,Cambie, Richard C.,Rutledge, Peter S.,Woodgate, Paul D.. "Experiments Directed Towards the Synthesis of Anthracyclinones. XII Preparation of a Substituted Isobenzofuran from an Anthradifuran". . p. 2075 - 2088. Retrieved 2007/10/02.