CAS
611-07-4 Purity
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611-07-4 Purity
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5-Nitroisatin
CAS
611-09-6
Catalog Number
ACM611096
Category
Other Products
Molecular Weight
192.13
Molecular Formula
C8H4N2O4
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- Product Description
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- Synthetic Use
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5-Nitroisatin for the Antimicrobial Enhancement of PLA/CCNC Nanocomposites
Ng WK, et al. Food Packaging and Shelf Life, 2021, 30, 100763.
This study investigated the incorporation of 5-nitroisatin (NI) as a hybrid antimicrobial agent with silver nanoparticles (AgNP) in poly(lactic acid)/corn cob nanocellulose (PLA/CCNC) nanocomposite films. The nanocomposites were prepared via a solvent casting method, using a fixed PLA/CCNC ratio of 95/5 based on prior optimization of mechanical and structural performance. AgNP loading was maintained at 5 phr, identified as the optimal concentration with acceptable ion migration, while aggregation was noted at higher levels. To evaluate partial substitution, films containing 5 phr NI and hybrid films containing 2.5 phr AgNP and 2.5 phr NI were prepared under identical conditions. Antimicrobial performance was assessed through agar disc diffusion and plastic surface inhibition assays. Results showed that PLA/CCNC-5/Ag/NI exhibited larger inhibition zones compared with PLA/CCNC-5/Ag and PLA/CCNC-5/NI, confirming the synergistic antimicrobial action of NI and AgNP within the PLA nanocomposite system.
5-Nitroisatin in the Synthesis of Chitosan-Based Schiff Base and Metal Complexes
Marjan Nasrabadi M, et al. International Journal of Biological Macromolecules, 2020,147, 534-546.
The experimental utility of 5-nitroisatin is exemplified in the preparation of functionalized chitosan derivatives through Schiff base chemistry. Initially, chitosan was refluxed in methanol, followed by the addition of 5-nitroisatin, yielding a yellow CSB Schiff base precipitate with a decomposition point of 220.1 °C and 65% yield. This intermediate served as a versatile ligand for transition-metal coordination. The Cu(II) complex was obtained by dropwise addition of CuCl₂·2H₂O in methanol to the CSB Schiff base solution at 40 °C, producing a dark-green solid decomposing at 200.8 °C with 78% yield. In parallel, Ni(II) complexation was achieved by reacting NiCl₂·6H₂O in DMF with the CSB Schiff base under reflux for 7 h, affording a light-green precipitate. These protocols highlight 5-nitroisatin's experimental role in Schiff base functionalization, enabling metal coordination for potential applications in catalysis, coordination chemistry, and biomaterial development.
5-Nitroisatin Conversion for the Synthesis of 5-Nitroindole Derivatives
Torisawa Y, et al. Bioorganic & Medicinal Chemistry Letters, 2001, 11(6), 829-832.
The transformation of 5-nitroisatin into 5-nitroindole derivatives has been demonstrated through an efficient reductive strategy employing the Itsuno system, a ZrCl₄/NaBH₄ mixed borohydride reagent in DME. Conventional reductants such as Red-Al or NaBH₄ alone resulted in undesirable nucleophilic ring-opening of the isatin core, yielding only modest amounts of unstable byproducts. To circumvent this instability, a crucial N-alkylation step was first introduced. Using CuCO₃/Cs₂CO₃ in anhydrous DMF, the team achieved mild and selective N-alkylation, avoiding base-induced degradation while forming stable intermediates such as N-(3-chloropropyl)-5-nitroisatin. Subsequent application of the Itsuno reducing system afforded rapid and direct cyclization to the nitroindole nucleus with high efficiency. The key role of ZrCl₄ was attributed to enhanced hydride transfer and suppression of side reactions. This methodology underscores the significance of reagent choice and pre-functionalization in manipulating base-labile heteroaromatic substrates.
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