3-Aminocoumarin

Base Information

• Chemical Name: 3-Aminocoumarin
• CAS No.: 1635-31-0
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29322010
• European Community (EC) Number: 216-659-4
• UNII: PC6801C293
• DSSTox Substance ID: DTXSID60167603
• Nikkaji Number: J80.269G
• Wikidata: Q72435031
• Metabolomics Workbench ID: 73964
• ChEMBL ID: CHEMBL1312108
• Mol file: 1635-31-0.mol

Synonyms:3-Aminocoumarin;3-amino-2H-chromen-2-one;1635-31-0;3-aminochromen-2-one;3-Amino-2-benzopyrone;3-Amino-2H-1-benzopyran-2-one;EINECS 216-659-4;2H-1-benzopyran-2-one, 3-amino-;PC6801C293;coumarin amine;MLS000532598;coumarin monoamine;3-azanylchromen-2-one;3-Aminocoumarin, 97%;Oprea1_066898;SCHEMBL95179;3-amino-1-benzopyran-2-one;CHEMBL1312108;UNII-PC6801C293;DTXSID60167603;3-amino-2-oxo-2H-1-benzopyran;3-AMINO-1,2-BENZOPYRONE;HMS2178H11;AMY15166;BCP20024;MFCD00016965;STK364532;AKOS001684142;NCGC00245539-01;SMR000137537;TS-02139;FT-0615035;EN300-235650;A810483;AN-829/06063010;W-201485;F2135-0511

Chemical Property of 3-Aminocoumarin

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 3.17E-05mmHg at 25°C
• Melting Point: 135-139 °C(lit.)
• Refractive Index: 1.624
• Boiling Point: 355.242 °C at 760 mmHg
• PKA: 3.22±0.20(Predicted)
• Flash Point: 199.282 °C
• PSA: 56.23000
• Density: 1.314 g/cm³
• LogP: 1.95640
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 235

Purity/Quality:

97% ^*data from raw suppliers

3-Amino-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)N
• General Description: 3-Aminocoumarin is a biologically and pharmaceutically significant compound that serves as a versatile scaffold in medicinal chemistry. It is synthesized via a copper(I)-catalyzed reaction involving salicylaldehyde, ethyl isocyanoacetate, and 2-aminopyridine, yielding derivatives with potential applications as CNS depressants, antitumor agents, anti-inflammatory drugs, antimicrobial compounds, and fluorescent markers. Its structural framework is considered a "privileged structure" in pharmaceutical and agrochemical research due to its broad utility and ease of functionalization.

Technology Process of 3-Aminocoumarin

There total 28 articles about 3-Aminocoumarin 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: 100.0%

(2-oxo-2H-chromen-3-yl)carbamic acid tert-butyl ester (205239-07-2) → aminocoumarine (1635-31-0)

Guidance literature:

With hydrogenchloride; In chloroform;

DOI:10.1002/jhet.5570350122

Reference yield: 98.0%

1-(2-oxo-4a,8a-dihydro-2H-chromen-3-yl)pyridinium chloride → aminocoumarine (1635-31-0)

Guidance literature:

With 1-methyl-piperazine; In acetone; at 20 ℃;

DOI:10.1016/j.tet.2014.05.074

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

upstream raw materials:

3-acetamidocoumarin

1-thiopropane

3-azido-2H-chromen-2-one

3-benzamidocoumarin

Downstream raw materials:

3-(N-tosyl-L-Ala)aminocoumarin

3-(N-Tosyl-DL-Ala)aminocoumarin

Boc-Phe-NH-c

3-(N-tosyl-DL-Ser)aminocoumarin

Refernces

Simple and efficient copper(I)-catalyzed access to three versatile aminocoumarin-based scaffolds using isocyanoacetate

10.1002/adsc.201000895

The study presents an efficient method for the one-pot copper(I)-catalyzed synthesis of 3-aminocoumarin and its derivatives, which are biologically and pharmaceutically significant compounds. The researchers utilized salicylaldehyde, ethyl isocyanoacetate, and 2-aminopyridine as the primary starting materials, along with copper(I) salts (CuI, Cu(OTf)2, etc.) as catalysts, and pyridine as a base. These chemicals served to construct molecular scaffolds that are valuable in medicinal chemistry due to their potential applications as CNS depressants, antitumor, anti-inflammatory, and antimicrobial agents, as well as their use as fluorescent markers. The study aimed to develop a straightforward and efficient approach to these molecular scaffolds, which are considered "privileged structures" in the pharmaceutical and agrochemical industries.