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Sodium tetraphenylborate is used as a precipitating reagent for potassium and as a protecting agent to protect amino acids. It is used in the preparation of N-acylammonium salts. It finds application as a phenyl donor in palladium-catalyzed cross-coupling reactions to prepare arylalkenes and biaryl compounds. It is used in inorganic and organometallic chemistry due to its solubility in nonpolar solvents. Furthermore, it is involved in the isolation of complexes having dinitrogen ligands.
Reagent for potassium by precipitation: Anal. Chem., 29, 1044 (1957).
Has been used to protect amino acids by formation of a diphenylborinate chelate, stable to AcOH or TFA, but cleaved by base: Tetrahedron, 39, 2995 (1983); Liebigs Ann. Chem., 127 (1989):
The cross coupling of tetraphenylborates or aryl boronic acids with aryl halides is catalyzed by Pd(OAc)2 in aqueous solutions: Dokl. Chem. (Engl. Transl.), 315, 354 (1990); see also: Gazz. Chem. Ital., 120, 779 (1990). Cross couples with vinyl and aryl triflates under Pd catalysis: Tetrahedron Lett., 35, 4835 (1992); 33, 4815 (1992). Similarly, allyl acetates are phenylated: Tetrahedron Lett., 31, 7453 (1990).
Howa, J. D.; Lott, M. J.; Ehleringer, J. R. Isolation and stable nitrogen isotope analysis of ammonium ions in ammonium nitrate prills using sodium tetraphenylborate. Rapid Commun. Mass Spectrom. 2014, 28 (13), 1530-1534.
Boruń, A.; Trzcińska, I.; Bald, A. Conductometric Studies of Sodium Iodide, Sodium Tetraphenylborate, Tetrabutylammonium Iodide, and Sodium Tetrafluoroborate in 1-Propanol at Temperatures from (283.15 to 318.15) K. Int. J. Electrochem. Sci. 2014, 9, 7805-7818.
Hazard Statements: H301-H315-H319-H335
Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant