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Nitrosonium tetrafluoroborate is a nitrosating agent and oxidizer used in organic synthesis. It is also used to convert arylamines directly to diazonium tetrafluoroborates, which undergo the Balz-Schiemann reaction in situ to give high yields of aryl fluorides. Further, it is used as a catalyst for iodination of aromatics by iodide ion with air as oxidant, conversion of secondary amines to nitrosamines and in deamination of primary amides. It is involved in the conversion of arylhydrazines to azides. In addition to this, it reacts with ferrocene to prepare ferrocenium tetrafluoroborate.
Crystalline nitrosating agent: Secondary amines to nitrosamines: Chem. Ber., 89, 2374 (1956); deamination of primary amides: J. Org. Chem., 30, 2386 (1965); conversion of arylhydrazines to azides: Tetrahedron Lett., 28, 5091 (1987). In organic solvents, converts arylamines directly to diazonium tetrafluoroborates which undergo the Balz-Schiemann reaction (see Tetrafluoroboric acid, L14037 ) in situ to give high yields of aryl fluorides: Chem. Ber., 88, 1939 (1955); EP 430,434 (1991). Methyl or methoxy substituted aromatics in acetonitrile give the nitrosoaromatics in good yield: J. Org. Chem., 59, 5573 (1994).
Convenient catalyst for iodination of aromatics by iodide ion with air as oxidant: J. Org. Chem., 53, 3548 (1988), or for addition of iodine (or iodine + nucleophile) to alkenes: Acta Chem. Scand. B, 43, 902 (1989).
Undergoes an interesting insertion reaction with diarylcyclopropanes: Chem. Lett., 233 (1988):
With excess reagent, oxidation of the isoxazoline to the isoxazole occurs.
Yang, Y.; Yao, Y.; He, L.; Zhong, Y.; Ma, Y.; Yao, J. Nonaqueous synthesis of TiO2-carbon hybrid nanomaterials with enhanced stable photocatalytic hydrogen production activity. J. Mater. Chem. A 2015, 3 (18), 10060-10068.
Bandi, V.; Gobeze, H. B.; Lakshmi, V.; Ravikanth, M.; DSouza, F. Vectorial Charge Separation and Selective Triplet-State Formation during Charge Recombination in a Pyrrolyl-Bridged BODIPY-Fullerene Dyad. J. Phys. Chem. C 2015, 119 (15), 8095-8102.
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.