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Sigma-Aldrich

2-Amino-3-formylchromone

97%

Sinónimos:

2-Amino-4-oxo-4H-1-benzopyran-3-carboxaldehyde

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About This Item

Fórmula empírica (notación de Hill):
C10H7NO3
Número de CAS:
61424-76-8
Peso molecular:
189.17
MDL number:
MFCD00191735
UNSPSC Code:
12352100
PubChem Substance ID:
24865040
NACRES:
NA.22

assay

97%

mp

249 °C (dec.) (lit.)

SMILES string

[H]C(=O)C1=C(N)Oc2ccccc2C1=O

InChI

1S/C10H7NO3/c11-10-7(5-12)9(13)6-3-1-2-4-8(6)14-10/h1-5H,11H2

InChI key

TVGIYZVZBKAJRR-UHFFFAOYSA-N

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
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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