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383473

Sigma-Aldrich

3-Formyl-6-methylchromone

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H8O3
CAS Number:
Molecular Weight:
188.18
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

mp

172-173 °C (lit.)

SMILES string

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

InChI key

GBWMIOYSMWCYIZ-UHFFFAOYSA-N

General description

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Enthalpies of combustion and formation of 3-formylchromones.
Flores H, et al.
Thermochimica Acta, 450(1), 35-37 (2006)
Jessica Elizabeth Philip et al.
Journal of photochemistry and photobiology. B, Biology, 175, 178-191 (2017-09-12)
Two chromone hydrazone ligands HL

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