5-Fluoroisatin

CAS Number 443-69-6

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

A fluorinated heterocyclic building block

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

Overview
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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

For facile synthesis

Fluorinated isatin building block

For drug discovery, catalysts, and OLEDs

Worldwide shipping

Quick and reliable shipping

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

Product Details

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

MSDS Documentation

5-Fluoroisatin MSDS Sheet

Literature and Reviews

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.
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.
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.
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.
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.

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