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Product Code B3401-100mg
Price $63 ex. VAT

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A fluorinated coumarin building block

As a synthesis intermediate for APIs


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

Multiple functional groups

For facile synthesis

Fluorinated coumarin building block

Fluorinated coumarin building block

For drug discovery, medicinal chemistry, and organic synthesis

competitively priced 2145-27-9

Low Cost

Competitively priced, high quality product

High purity 2145-27-9

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

7-Fluoro-4-hydroxycoumarin chemical structure, CAS number 2145-27-9
7-Fluoro-4-hydroxycoumarin chemical structure, CAS number 2145-27-9

Product Details

Purity 98%
Melting Point Tm = 220 °C – 225 °C
Appearance Off-white powder

MSDS Documentation

7-Fluoro-4-hydroxycoumarin7-Fluoro-4-hydroxycoumarin MSDS Sheet

Literature and Reviews

  1. 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.
  2. 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.
  3. 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.
  4. Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: quinone oxidoreductase-1 (NQO1), K. Nolan et al., J. Med. Chem., 52 (22), 7142–7156 (2009); DOI: 10.1021/jm9011609.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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