2-Amino-3-formylchromone

Base Information

• Chemical Name: 2-Amino-3-formylchromone
• CAS No.: 61424-76-8
• Molecular Formula: C10H7NO3
• Molecular Weight: 189.17
• Hs Code.: 2922509090
• European Community (EC) Number: 624-966-3
• DSSTox Substance ID: DTXSID50352884
• Nikkaji Number: J1.869.084E
• Wikidata: Q82130291
• ChEMBL ID: CHEMBL87426
• Mol file: 61424-76-8.mol

Synonyms:2-aminochromone-3-carboxaldehyde

Chemical Property of 2-Amino-3-formylchromone

Chemical Property:

• Vapor Pressure: 1.2E-06mmHg at 25°C
• Melting Point: 249oC (dec.)(lit.)
• Boiling Point: 401.2°C at 760 mmHg
• PKA: 1.31±0.20(Predicted)
• Flash Point: 241°C
• PSA: 73.30000
• Density: 1.486g/cm³
• LogP: 1.76890
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 189.042593085
• Heavy Atom Count: 14
• Complexity: 309

Purity/Quality:

97% ^*data from raw suppliers

2-Amino-3-formylchromone ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C(=C(O2)N)C=O
• General Description: 2-Amino-3-formylchromone is a versatile heterocyclic compound used as a key intermediate in the synthesis of novel Schiff bases with antimicrobial properties. Its structure, featuring an amino group and a formyl substituent on the chromone scaffold, enables condensation reactions with hydrazine derivatives to form azomethine-linked heterocyclic systems. These derivatives, particularly those incorporating 1,2,4-triazole or 1,2,4-triazine moieties, demonstrate significant antimicrobial activity against bacteria and fungi, highlighting 2-AMINO-3-FORMYLCHROMONE's potential in developing new therapeutic agents. Further structural modifications could optimize its biological efficacy.

Technology Process of 2-Amino-3-formylchromone

There total 1 articles about 2-Amino-3-formylchromone 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: 45.0%

4-oxo-4H-1-benzopyran-3-carbonitrile (50743-17-4) + ethylenediamine (107-15-3,85404-18-8) → 2-amino-3-formylchromone (61424-76-8) + 2-<(2-hydroxybenzoyl)methylene>-1,3,4,5-tetrahydroimidazole (73262-05-2)

Guidance literature:

In ethanol; for 3h; Heating;

DOI:10.1021/jo01298a042

Reference yield: 95.0%

2-amino-3-formylchromone (61424-76-8) + ethyl acetoacetate (141-97-9) + phenylhydrazine (100-63-0) → (Z)-4-((2-amino-4-oxo-4H-chromen-3-yl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Guidance literature:

With silica-supported zinc bromide (SiO₂/ZnBr₂); In water; at 60 ℃; for 0.25h; Microwave irradiation; Green chemistry;

DOI:10.1039/c5ra21146h

Reference yield: 90.0%

2-amino-3-formylchromone (61424-76-8) + p-chlorobenzoylacetonitrile (4640-66-8) → 2-(4-chlorophenyl)-5-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile (869637-43-4)

Guidance literature:

With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 100 ℃; for 16h;

DOI:10.3987/com-07-11128

upstream raw materials:

4-oxo-4H-1-benzopyran-3-carbonitrile

ethylenediamine

Downstream raw materials:

3-phenyl-3H-chromeno[2,3-d]pyrimidine-2,5-dione

2-amino-5-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile

2-amino-4H-1-benzopyran-4-one

4-hydroxy[1]benzopyran-2-one

Refernces

Synthesis and antimicrobial activity of some new heterocyclic schiff bases derived from 2-Amino-3-formylchromone

10.1080/10426500802625594

The research aimed to synthesize new heterocyclic Schiff bases derived from 2-amino-3-formylchromone and investigate their antimicrobial activity. The study focused on combining chromone moieties with 1,2,4-triazole or 1,2,4-triazine derivatives through an azomethine linkage to create novel nitrogen heterocyclic systems. Key chemicals used included 2-amino-3-formylchromone as the starting material, various hydrazine derivatives (such as benzoylhydrazine, cyanoacetohydrazide, and thiocarbohydrazide) for condensation reactions, and electrophilic reagents like benzoyl chloride, acetic anhydride, and carbon disulfide for further heterocyclization. The newly synthesized compounds were characterized using IR, 1H NMR, and mass spectrometry. The antimicrobial activity of these compounds was tested against a range of bacteria and fungi, revealing that compounds 8 and 20 showed moderate activity against bacteria and high activity against fungi, while compounds 9, 13, and 15 exhibited high antifungal activity. The study concluded that the synthesized compounds have potential as antimicrobial agents, particularly those incorporating dithioxo-1,2,4-triazole and antipyrine moieties, and suggested that further modifications could enhance their biological efficacy.

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