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383473

Sigma-Aldrich

3-Formyl-6-methylchromone

97%

Synonyme(s) :

6-Methyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde

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About This Item

Formule empirique (notation de Hill):
C11H8O3
Numéro CAS:
42059-81-4
Poids moléculaire :
188.18
Numéro MDL:
MFCD00138943
Code UNSPSC :
12352100
ID de substance PubChem :
24863971
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

solid

Pf

172-173 °C (lit.)

Chaîne SMILES 

Cc1ccc2OC=C(C=O)C(=O)c2c1

InChI

1S/C11H8O3/c1-7-2-3-10-9(4-7)11(13)8(5-12)6-14-10/h2-6H,1H3

Clé InChI

GBWMIOYSMWCYIZ-UHFFFAOYSA-N

Catégories apparentées

Description générale

3-Formyl-6-methylchromone is a 3-formyl-substituted chromone. The combustion calorimetric estimation of the enthalpy of combustion of 3-formyl-6-methylchromone has been reported. Its anti-proliferative action on the MDR human colon cancer and mouse lymphoma has been investigated.

Application

3-Formyl-6-methylchromone has been used for the synthesis of 3-formyl-6-methylchromone-4-phenylthiosemicarbazone.
3-Formyl-6-methylchromone may be used in the preparation of series of Schiff′s bases, via reaction with aromatic sulfonamides, such as sulfanilamide, homosulfanilamide, 4-aminoethyl-benzenesulfonamide, a pyrimidinyl-substituted sulfanilamide derivative, sulfaguanidine and 4-amino-6-trifluoromethyl-benzene-1,3-disulfonamide. It may be used in the preparation of Schiff base, which undergoes addition reaction with diethyl phosphite to afford bis[(1,2,4,3-triazaphospholyl)(chromonyl)aminomethylphosphonate] derivative and bis[(1,2,4,3-triazaphospholyl)(chromonyl)phosphorylamino-methylphosphonate] derivative.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Synthesis, characterization, crystal structure and antimicrobial activity of copper (II) complexes with a thiosemicarbazone derived from 3-formyl-6-methylchromone.
Ilies DC, et al.
Polyhedron, 81, 123-131 (2014)
Luca Puccetti et al.
Bioorganic & medicinal chemistry letters, 15(12), 3096-3101 (2005-05-24)
A series of Schiff's bases was prepared by reaction of 3-formyl-chromone or 6-methyl-3-formyl-chromone with aromatic sulfonamides, such as sulfanilamide, homosulfanilamide, 4-aminoethyl-benzenesulfonamide, a pyrimidinyl-substituted sulfanilamide derivative, sulfaguanidine and 4-amino-6-trifluoromethyl-benzene-1,3-disulfonamide. The zinc complexes of these sulfonamides have also been obtained. The new
Synthetic approach for novel bis (a-aminophosphonic acid) derivatives of chromone containing 1, 2, 4, 3-triazaphosphole moieties
Ali, TE and Halacheva, SS.
Heteroatom Chem., 20(3), 117-122 (2009)
Jessica Elizabeth Philip et al.
Journal of photochemistry and photobiology. B, Biology, 175, 178-191 (2017-09-12)
Two chromone hydrazone ligands HL
Farukh Arjmand et al.
Bioorganic chemistry, 104, 104327-104327 (2020-11-05)
Copper-based antitumor drug entities 1-3 derived from substituted (F-, Br-, -CH3) 3-formylchromone pharmacophore were synthesized and thoroughly characterized by spectroscopic and single X-ray crystallographic studies. These complexes show structural novelty due to presence of the X-bonds in chromone scaffold which
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