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.
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Applications
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.
Solubility
Soluble in acetonitrile.
Notes
Hygroscopic. Air and moisture sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and amines.
RUO – Research Use Only
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.
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