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Product Code B3401-100mg
Price £50 ex. VAT

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.
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