2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione

Base Information

• Chemical Name: 2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione
• CAS No.: 114479-07-1
• Molecular Formula: C17H13NO2
• Molecular Weight: 263.296
• DSSTox Substance ID: DTXSID70550325
• Nikkaji Number: J3.332.333F
• Wikidata: Q82429608
• Mol file: 114479-07-1.mol

Synonyms:114479-07-1;2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione;DTXSID70550325;2-Amino-3-(p-tolyl)naphthalene-1,4-dione

Chemical Property of 2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 263.094628657
• Heavy Atom Count: 20
• Complexity: 458

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3C2=O)N

Technology Process of 2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione

There total 4 articles about 2-Amino-3-(4-methylphenyl)naphthalene-1,4-dione 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: 79.0%

2-(4-methyl-benzylidene)-indan-1,3-dione (15875-51-1) → 2-amino-3-(4-methylphenyl)-1,4-naphthoquinone (114479-07-1)

Guidance literature:

With sodium azide; acetic acid; In dimethyl sulfoxide; at 20 ℃; for 5h;

Reference yield: 62.0%

2-amino-1,4-naphthoquinone (2348-81-4) + N-4-methylphenylhydrazine (539-44-6) → 2-amino-3-(4-methylphenyl)-1,4-naphthoquinone (114479-07-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In acetonitrile; at 20 ℃;

DOI:10.1021/jo500131h

Reference yield:

2-amino-1,4-naphthoquinone (2348-81-4) → 2-amino-3-(4-methylphenyl)-1,4-naphthoquinone (114479-07-1)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodomorpholine-hydrogen iodide; potassium carbonate / water

2: potassium carbonate; palladium diacetate / water; ethanol / 0.5 h / 100 °C / Microwave irradiation

With palladium diacetate; N-iodomorpholine-hydrogen iodide; potassium carbonate; In ethanol; water; 2: |Suzuki Coupling;

DOI:10.1016/j.bioorg.2020.104278

upstream raw materials:

2-(4-methyl-benzylidene)-indan-1,3-dione

2-amino-1,4-naphthoquinone

N-4-methylphenylhydrazine

[1,4]naphthoquinone