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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-H315-H319-H335-H373
May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P220-P221-P261-P262-P264b-P271-P280i-P281-P302+P352-P304+P340-P305+P351+P338-P308+P313-P332+P313-P337+P313-P362-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear eye/face protection. Use personal protective equipment as required. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. If skin irritation occurs: If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant