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3-Cyanochromon
97%
Synonym(e):
4-Oxo-4H-1-benzopyran-3-carbonitril
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About This Item
Empirische Formel (Hill-System):
C10H5NO2
CAS-Nummer:
Molekulargewicht:
171.15
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22
Empfohlene Produkte
Qualitätsniveau
Assay
97%
mp (Schmelzpunkt)
174-176 °C (lit.)
Funktionelle Gruppe
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
InChIKey
SFWNPLLGXKJESA-UHFFFAOYSA-N
Verwandte Kategorien
Allgemeine Beschreibung
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.
Anwendung
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
Signalwort
Danger
H-Sätze
Gefahreneinstufungen
Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation
Lagerklassenschlüssel
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
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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)
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)
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)
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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