402028
2-Amino-3-formylchromone
97%
Synonym(s):
2-Amino-4-oxo-4H-1-benzopyran-3-carboxaldehyde
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About This Item
Empirical Formula (Hill Notation):
C10H7NO3
CAS Number:
Molecular Weight:
189.17
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
InChI
1S/C10H7NO3/c11-10-7(5-12)9(13)6-3-1-2-4-8(6)14-10/h1-5H,11H2
SMILES string
[H]C(=O)C1=C(N)Oc2ccccc2C1=O
InChI key
TVGIYZVZBKAJRR-UHFFFAOYSA-N
assay
97%
mp
249 °C (dec.) (lit.)
functional group
aldehyde, ketone
Quality Level
Gene Information
human ... PTPN1(5770)
General description
2-Amino-3-formylchromone (2-Amino-4-oxo-4H-1-benzopyran-3-carboxaldehyde) is a benzopyran derivative. It is a bicyclic heterocyclic molecule made up of a benzene ring fused to a heterocyclic pyran ring. It undergoes condensation with (R)-2-amino-2-phenylethanol to afford Schiff base ligand, which forms complexes with Cu(NO3)2 and Zn(NO3)2.
Application
2-Amino-3-formylchromone may be used in the preparation of the following:
- chiral Schiff base ligands (R)/(S)-2-amino-3-(((1-hydroxypropan-2-yl)imino)methyl)-4H-chromen-4-one
- hydrazone derivatives, required for the synthesis of heterocyclic Schiff′s bases having antimicrobial activity
- N-{4-[(6-chloro-4-oxo-4H-chromen-3-ylmethylene)amino]phenyl}-3,5-dimethyl-benzofuran-2-carboxamide
- N-{4-[(6-chloro-4-oxo-4H-chromen-3-ylmethylene)amino]phenyl}-1,4-dihydro-chromono [2,3-b]pyrrole-2-carboxamide
- 6-chloro-3-{[4-(2-thioxo-3,6-dihydro-2H-1,3,4-thiadiazin-5-ylamino)phenylimino] methyl}- 4-oxo-4H -chromene
- 3-(2-amino-4-oxo-4H-chromen-3-yl)methylidene)-6- ethyl-2H-pyrano[3,2-c]quinolone-2,4,5(3H,6H)trione
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Synthesis and antimicrobial activity of some new heterocyclic Schiff bases derived from 2-amino-3-formylchromone.
Ibrahim MA and El-Mahdy KM.
Phosphorus, Sulfur, and Silicon and the Related Elements, 184(11), 2945-2958 (2009)
Synthesis of some new 4-oxo-4H-chromene derivatives bearing nitrogen heterocyclic systems as antifungal agents.
Ali T E-S, et al.
Turkish Journal of Chemistry, 32(3), 365-374 (2008)
Novel heterocyclic derivatives of pyrano [3, 2-c] quinolinone from 3-(1-ethy1-4-hydroxy-2-oxo-2 (1H)-quinolin-3-yl)-3-oxopropanoic acid.
Ibrahim MA, et al.
European Journal of Chemistry, 1(3), 195-199 (2010)
Farukh Arjmand et al.
Chirality, 24(12), 977-986 (2012-09-25)
Novel chiral Schiff base ligands (R)/(S)-2-amino-3-(((1-hydroxypropan-2-yl)imino)methyl)-4H-chromen-4-one (L(1) and L(2)) derived from 2-amino-3-formylchromone and (R/S)-2-amino-1-propanol and their Cu(II)/Zn(II) complexes (R1, S1, R2, and S2) were synthesized. The complexes were characterized by elemental analysis, infrared (IR), hydrogen ((1) H) and carbon ((13)C)
Farukh Arjmand et al.
Journal of photochemistry and photobiology. B, Biology, 103(2), 166-179 (2011-04-05)
New Schiff base ligand L derived from the condensation reaction of 2-amino-3-formylchromone with (R)-2-amino-2-phenylethanol was synthesized and characterized which involves combination element of ammine functionality and naturally occurring heterocyclic chromone, 4H-benzopyran-4-one. Subsequently, their complexes 1 and 2 with Cu(NO₃)₂ and
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