7-Fluoro-4-hydroxycoumarin

CAS Number 2145-27-9

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Monomers

7-Fluoro-4-hydroxycoumarin CAS 2145-27-9

A fluorinated coumarin building block

As a synthesis intermediate for APIs

Overview
Related Products

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	T_m = 220 °C – 225 °C
Appearance	Off-white powder

MSDS Documentation

7-Fluoro-4-hydroxycoumarin MSDS Sheet

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.
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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