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Product Code B1761-25g
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A fluorinated heterocyclic building block

Used as a synthesis intermediate for Schiff bases, macromolecules, and metal complexes in application of catalysts, OLEDs, and APIs

5-Fluoroisatin (CAS number 443-69-6), a fluorinated indole derivative, contains a fluorine (5-position) and two carbonyls (2,3-positions). The carbonyl group at 3-position reacts with amines or hydrazines for imines or hydrazones that function as Schiff bases. The Schiff base based on 5-fluoroisatin coordinates to cobalt, yielding Co-isatin complexes. The metal complexes catalyse oxidative condensation reaction in air by generating singlet oxygen under sunlight. A macromolecule with donor-acceptor-donor system can be synthesized with 5-fluoroisatin and a diamine building block. The OLED device based on the macromolecule shows external quantum efficiency of 0.0515% with emission of 630 to 700 nm.

The 5-membered ring of 5-fluoroisatin can be expanded, forming isatoic anhydride through Baeyer-Villiger oxidation with mCPBA (meta-chloroperoxybenzoic acid). 5-Fluoroisatin can also be reshaped to a quinoline under Pfitzinger reaction, providing a platform for post-modification of the isatin derivatives.

Multiple functional groups

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated isatin building block

For drug discovery, catalysts, and OLEDs

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High purity 443-69-6

High purity

>98% High purity

General Information

CAS Number 443-69-6
Chemical Formula C8H4FNO2
Full Name 5-Fluoro-1H-indole-2,3-dione
Molecular Weight 165.12 g/mol
Synonyms 5-Fluoro-2,3-indoledione, 5-Fluoroindole-2,3-dione, NSC 39161
Classification / Family Fluorinated building block, Heterocyclic building block, APIs, Catalysts, OLEDs

Chemical Structure

5-Fluoroisatin chemical structure, CAS 443-69-6
5-Fluoroisatin chemical structure, CAS 443-69-6

Product Details

Purity 98%
Melting Point Tm = 224 °C – 227 °C
Appearance Deep red powder

MSDS Documentation

5-Fluoroisatin MSDS Sheet5-Fluoroisatin MSDS Sheet

Literature and Reviews

  1. Cobalt isatin‑Schiff‑base derivative of MOF as a heterogeneous multifunctional bio‑photocatalyst for sunlight‑induced tandem air oxidation condensation process, M. Rouzifar et al., Sci. Rep., 13, 515(2023); DOI: 10.1038/s41598-023-32241-z.
  2. Computational evaluation and experimental in vitro antibacterial, antifungal and antiviral activity of bis-Schiff bases of isatin and its derivatives, A. Jarrahpour et al., Med. Chem. Res., 22, 1203–1211(2013); DOI: 10.1007/s00044-012-0127-6.
  3. Recyclable (PhSe)2-Catalyzed selective oxidation of isatin by H2O2: a practical and waste-free access to isatoic anhydride under mile and neutral conditions, L. Yu et al., Catal. Sci. Technol., 5, 4830–4838(2015); DOI: 10.1039/C5CY01030F.
  4. Near infrared organic light-emitting diodes based on acceptor–donor–acceptor (ADA) using novel conjugated isatin Schiff bases, M. Sharbati et al., J. Lumin., 13, 135–138(2011); DOI: 10.1016/j.jlumin.2010.10.016.
  5. Synthesis, biological activity and docking study of some new isatin Schiff base derivatives, J. Azizian et al., Med. Chem. Rev., 21, 3730–3740(2012); DOI: 10.1007/s00044-011-9896-6.

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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