3-Nitrocoumarin

Base Information

• Chemical Name: 3-Nitrocoumarin
• CAS No.: 28448-04-6
• Molecular Formula: C9H5NO4
• Molecular Weight: 191.143
• European Community (EC) Number: 877-970-4
• UNII: UT6T82NTW8
• DSSTox Substance ID: DTXSID10384106
• Nikkaji Number: J601.992G
• Wikidata: Q82176040
• ChEMBL ID: CHEMBL70729
• Mol file: 28448-04-6.mol

Synonyms:3-nitrocoumarin

Chemical Property of 3-Nitrocoumarin

Chemical Property:

• PSA: 76.03000
• LogP: 2.22440
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 191.02185764
• Heavy Atom Count: 14
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

3-Nitrocoumarin 100% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)[N+](=O)[O-]

Technology Process of 3-Nitrocoumarin

There total 1 articles about 3-Nitrocoumarin 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: 34.0%

N-methyl-N-[4-(methylsulfanyl)-3-nitro-4H-chromen-2-yl]amine (1173429-43-0) + phenylboronic acid (98-80-6) → 3-nitrocoumarin (28448-04-6) + N-methyl-3-nitro-4-phenyl-4H-chromen-2-amine (1629209-60-4)

Guidance literature:

With copper(II) acetate monohydrate; In N,N-dimethyl-formamide; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201402003

Reference yield: 95.0%

3-nitrocoumarin (28448-04-6) → aminocoumarine (1635-31-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; at 20 ℃; for 5h;

DOI:10.1111/j.2042-7158.2012.01467.x

Reference yield: 87.0%

3-nitrocoumarin (28448-04-6) + 5-hydroxy-2-((phenylthio)methyl)-4H-pyran-4-one (138426-83-2) → 4-(3-hydroxy-4-oxo-6-((phenylthio)methyl)-4H-pyran-2-yl)-2H-chromen-2-one

Guidance literature:

With triethylamine; In acetonitrile; for 4h; Reflux;

DOI:10.1016/j.tetlet.2021.152939

upstream raw materials:

N-methyl-N-[4-(methylsulfanyl)-3-nitro-4H-chromen-2-yl]amine

phenylboronic acid

Downstream raw materials:

1-benzofurane

β-(2-hydroxyphenyl)nitroethane

Refernces