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383481

Sigma-Aldrich

3-Cyanochromone

97%

Synonym(s):

4-Oxo-4H-1-benzopyran-3-carbonitrile

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About This Item

Empirical Formula (Hill Notation):
C10H5NO2
CAS Number:
50743-17-4
Molecular Weight:
171.15
MDL number:
MFCD00052604
UNSPSC Code:
12352100
PubChem Substance ID:
24863972
NACRES:
NA.22

Assay

97%

mp

174-176 °C (lit.)

functional group

ketone
nitrile

SMILES string

O=C1C(=COc2ccccc12)C#N

InChI

1S/C10H5NO2/c11-5-7-6-13-9-4-2-1-3-8(9)10(7)12/h1-4,6H

InChI key

SFWNPLLGXKJESA-UHFFFAOYSA-N

Related Categories

General description

3-Cyanochromone (4-Oxo-4H-1-benzopyran-3-carbonitrile), a 3-substituted chromone, is a cyano substituted 1-benzopyran-4-one. It is an α,β-unsaturated nitrile and also an α,β-unsaturated ketone. Its molecule has electron deficiency at 3 sites i.e C (carbon) at second position, C of cyano and carbonyl group. 2-Amino-3-(alkyliminomethyl)chromones are obtained as major products during its reaction with aliphatic amines.

Application

3-Cyanochromone may be used in the syntheses of following:
  • 2-aminochromone-3-carboxamide
  • 3-amino-4H-chromeno[3,4-d]isoxazol-4-one
  • 3-(diaminomethylene)chroman-2,4-dione
  • functionalized novel spirobenzofuranones
  • 6H-bis-[1]-benzopyrano[2,3-b:3′,4′-e]pyridin-8(8H)ones and 3-(2′-hydroxybenzoyl)-5H-[1]benzopyrano[4,3-b]pyridine

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H312 + H332

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV9352V
MKBP9679V
71597PJ
13031JZ
01202KU

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A reinvestigation of the reactions of 3-substituted chromones with hydroxylamine. Unexpected synthesis of 3-amino-4H-chromeno [3,4-d] isoxazol-4-one and 3-(diaminomethylene) chroman-2,4-dione.
Sosnovskikh VY, et al.
Tetrahedron Letters, 49(48), 6856-6859 (2008)
Chemistry of 4-oxo-4H-1-benzopyran-3-carbonitrile.
Ghosh CK and Karak SK.
Journal of Heterocyclic Chemistry, 42(6), 1035-1035 (2005)
Structural revision in the reactions of 3-cyanochromones with primary aromatic amines. Improved synthesis of 2-amino-3-(aryliminomethyl) chromones.
Sosnovskikh VY, et al.
Tetrahedron Letters, 50(47), 6515-6518 (2009)
SYNTHESIS OF 6 H-bis-[1]-BENZOPYRANO [2, 3-b: 3', 4'-e] PYRIDIN-8 (8 H) ONES AND 3-(2'-HYDROXYBENZOYL)-5 H-[1] BENZOPYRANO [4, 3-b] PYRIDINES AND THEIR DERIVATIVES.
Reddy KV, et al.
Organic preparations and procedures international, 28(3), 325-332 (1996)
Tryfon Zarganes-Tzitzikas et al.
The Journal of organic chemistry, 76(21), 9008-9014 (2011-10-14)
Another aspect concerning chromone chemistry leading to the one-pot synthesis of functionalized novel spirobenzofuranones has been described. The synthesis involves reaction of the zwitterionic intermediates formed by the 1:1 interaction between isocyanides and acetylenecarboxylates with 3-cyanochromones, whereupon through an unexpected

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