A fluorinated coumarin building block
As a synthesis intermediate for APIs
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7-Fluoro-4-hydroxycoumarin (CAS number 2145-27-9) is a derivative of coumarin with hydroxyl and fluoride groups at the 4- and 7-positions. Coumarin has a structure consisting of a benzene ring fused with a 2-pyrone known as benzopyrone, which is commonly found in many plants. 7-Fluoro-4-hydroxycoumarin is thus an ideal candidate as a natural product substrate in organic synthesis. The 3-position of 7-fluoro-4-hydroxycoumarin can be functionalised with unsaturated 2-ketoesters catalysed by chiral bisoxazoline−copper(II) complexes. This asymmetric Michael reaction demonstrates good yield with up to 98% enantiomeric excess (ee).
7-Fluoro-4-hydroxycoumarin is applied in the synthesis of chromeno[4,3-b]pyridinone derivatives which exhibit anticancer, antibacterial and antimicrobial activity. This solvent-free reaction consists of three components including 7-fluoro-4-hydroxycoumarin, ammonium acetate and 3-formylchromone. The reaction is catalysed by l-proline.
Multiple functional groups
For facile synthesis
Fluorinated coumarin building block
For drug discovery, medicinal chemistry, and organic synthesis
Low Cost
Competitively priced, high quality product
High purity
>98% High purity
General Information
| CAS Number | 2145-27-9 |
| Chemical Formula | C9H5FO3 |
| Full Name | 7-Fluoro-4-hydroxy-2H-chromen-2-one |
| Molecular Weight | 180.13 g/mol |
| Synonyms | 7-Fluoro-4-hydroxy-1(2H)-benzopyran-2-one |
| Classification / Family | Fluorinated building blocks, Coumarin building blocks, Heterocyclic building blocks, APIs, Organic synthesis |
Chemical Structure
Product Details
| Purity | 98% |
| Melting Point | Tm = 220 °C – 225 °C |
| Appearance | Off-white powder |
MSDS Documentation
Literature and Reviews
- Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline−copper(II) complexes, N. Halland et al., J. Org. Chem., 68 (13), 5067–5074 (2003); DOI: 10.1021/jo0343026.
- Eco-friendly construction of highly functionalized chromenopyridinones by an organocatalyzed solid-state melt reaction and their optical properties, S. Paul et al., Green Chem., 18, 1488–1494 (2016); DOI: 10.1039/C5GC02658J.
- A new protocol for total synthesis of natural product frutinone A and its derivatives, K. Lei et al., Aust. J. Chem., 69, 98–106 (2016); DOI: 10.1071/CH15267.
