5-Fluoroisatin (5-Fluoro-1H-indole-2,3-dione, CAS 443-69-6) is a fluorinated indole derivative supplied as a deep red powder with >98% purity. It carries a fluorine atom at the 5-position and carbonyl groups at the 2- and 3-positions, giving chemists several reactive sites for building Schiff bases, macromolecules and metal complexes aimed at catalysis, OLEDs and active pharmaceutical ingredients.
Its 3-position carbonyl condenses with amines or hydrazines to give imines or hydrazones that act as Schiff bases. A Schiff base derived from this compound binds cobalt to form Co-isatin complexes, which catalyse oxidative condensation in air by producing singlet oxygen under sunlight. Combined with a diamine building block, it yields a donor-acceptor-donor macromolecule; an OLED built on this material reached an external quantum efficiency of 0.0515% with emission from 630 to 700 nm.
The five-membered ring can also be expanded to isatoic anhydride by Baeyer-Villiger oxidation with mCPBA (meta-chloroperoxybenzoic acid), or converted into a quinoline through the Pfitzinger reaction, opening routes to further modification of isatin derivatives.
- Synthesis of Schiff bases (imines and hydrazones) from amines or hydrazines.
- Preparation of cobalt-isatin complexes for sunlight-driven oxidative condensation catalysis.
- Construction of donor-acceptor-donor macromolecules for red to near-infrared OLED emitters.
- Intermediate for drug discovery and API research.
- Ring expansion to isatoic anhydride or conversion to quinolines via the Pfitzinger reaction.
| Brand | Ossila |
|---|---|
| CAS number | 443-69-6 |
| Molecular formula | C8H4FNO2 |
| Purity | >98% |
| Category | — |
| Pack sizes | 25 g, 50 g |
| Physical form | Deep red powder |
| Storage | — |
- Product code: B1761
- 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
- Melting Point: 224 °C – 227 °C
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