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Bismuth(III) nitrate pentahydrate is an oxidant for a variety of 4-substituted Hantzsch 1,4-dihydropyridines. It also serves as a reagent for selective oxidation of sufides to sulfoxides. Further, it is involved in the preparation of Dragendorff reagent and used as a TLC stain. It is also used to prepare other bismuth compounds.
Useful, easily handled oxidizing and nitrating agent in organic synthesis. Montmorillonite KSF acidic clay impregnated with bismuth nitrate was found to be an excellent reagent for high-yield aromatic nitration: Tetrahedron Lett., 41, 8017 (2000). Phenols can be nitrated with the salt itself in acetone, or without solvent: J. Org. Chem., 70, 9071 (2005). In the presence of montmorillonite, alcohols can be oxidized to carbonyl compounds: Synth. Commun., 31, 2691 (2001). Reagent for deprotection of oximes: Synthesis, 1010 (2001), and hydrazones: Synth. Commun., 32, 1917 (2001). Thioamides and thioureas are readily converted to their oxo-analogs: Tetrahedron Lett., 44, 591 (2003).
Catalyst for a convenient, high-yield Michael addition of various substrates, including amines, imidazoles and indoles, to enones: J. Org. Chem., 68, 2109 (2003). Efficient catayst for tetrahydropyranylation and depyranylation of alcohols: Eur. J. Org. Chem., 4891 (2005).
For a brief feature on uses of the reagent in organic synthesis, see: Synlett, 2699 (2005).
Zahedifar, M.; Sheibani, H. Rapid three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of Bi(NO3)3·5H2O as a mild and highly efficient catalyst. Res. Chem. Intermed. 2015, 41 (1), 105-111.
Pei, C. C.; Leung, W. W. F. Photocatalytic oxidation of nitrogen monoxide and o-xylene by TiO2/ZnO/Bi2O3 nanofibers: Optimization, kinetic modeling and mechanisms. Appl. Catal., B 2015, 174, 515-525.
Hazard Statements: H272-H303-H315-H319-H335
May intensify fire; oxidizer. May be harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P221-P210v-P220-P305+P351+P338-P405-P501a
Take any precaution to avoid mixing with combustibles. Keep/Store away from clothing/combustible materials. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.