3-Acetamidophthalic acid

Base Information

• Chemical Name: 3-Acetamidophthalic acid
• CAS No.: 15371-06-9
• Molecular Formula: C10H9 N O5
• Molecular Weight: 223.185
• European Community (EC) Number: 239-404-9
• UNII: I1M6HR1N6D
• DSSTox Substance ID: DTXSID8065878
• Nikkaji Number: J218.410I
• Wikidata: Q27280255
• Mol file: 15371-06-9.mol

Synonyms:3-Acetamidophthalic acid;15371-06-9;3-(Acetylamino)phthalic acid;1,2-Benzenedicarboxylic acid, 3-(acetylamino)-;UNII-I1M6HR1N6D;I1M6HR1N6D;EINECS 239-404-9;3-Acetamido-1,2-benzenedicarboxylic acid;APREMILAST (M18);Oprea1_607739;Oprea1_724758;DTXSID8065878;SCHEMBL11593694;PHTHALIC ACID, 3-ACETAMIDO-;STK962881;AKOS028110890;AS-76832;CS-0010088;3-(acetylamino)benzene-1,2-dicarboxylic acid;D95551;3-ACETAMIDOBENZENE-1,2-DICARBOXYLIC ACID;Q27280255

Chemical Property of 3-Acetamidophthalic acid

Chemical Property:

• Vapor Pressure: 1.45E-11mmHg at 25°C
• Melting Point: 260 °C
• Boiling Point: 518.2°Cat760mmHg
• PKA: 2.54±0.10(Predicted)
• Flash Point: 267.2°C
• PSA: 107.19000
• Density: 1.512g/cm³
• LogP: 1.69090
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 223.04807239
• Heavy Atom Count: 16
• Complexity: 314

Purity/Quality:

99% ^*data from raw suppliers

3-AcetamidophthalicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC=CC(=C1C(=O)O)C(=O)O
• Uses: 3-Acetamidophthalic Acid is an impurity of Apremilast (A729700); an oral phosphodiesterase 4 inhibitor used in the treatment of psoriatic arthritis. Apremilast EP Impurity B

Technology Process of 3-Acetamidophthalic acid

There total 7 articles about 3-Acetamidophthalic 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:

3-aminophthalic acid (5434-20-8,857040-74-5) + acetyl chloride (75-36-5) → 3-acetylaminophthalic acid (15371-06-9)

Guidance literature:

With triethanolamine; In dichloromethane; at 0 - 5 ℃; for 1h;

DOI:10.14233/ajchem.2016.20109

Reference yield:

3-aminophthalic acid (5434-20-8,857040-74-5) + acetic anhydride (108-24-7) → 3-acetylaminophthalic acid (15371-06-9)

Guidance literature:

In water; at 15 - 20 ℃; for 2h;

Reference yield:

3-nitrophthalic acid (603-11-2) → 3-acetylaminophthalic acid (15371-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen; sodium hydroxide / water / 20 °C / 1500.15 Torr

2: water / 2 h / 15 - 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydroxide; In water;

upstream raw materials:

3-acetamidophthalimide

3-aminophthalic acid

acetyl chloride

3-nitrophthalic acid

Downstream raw materials:

Apremilast