ChemicalName:Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, sodium salt, dihydrate CAS: 79060-88-1
Appearance: White crystalline powder
Purity: ≥99.0% (Titration, as anhydrous))
MW: 886.20, C32H12BF24Na
Storage Condition: ambient temperature
Shipping Condition: ambient temperature
Tetraphenylborate is unstable in acidic conditions because protons attack the ipso-carbon of the phenyl group and benzene is released. However, the electron density of the ipso-carbon of TFPB is low due to a trifluoromethyl group. Thus TFPB is stable in acidic conditions (such as 50 mM sulfuric acid solution). TFPB is used in Friedel-Craft alkylation or diazo coupling reactions as a phase transfer reagent. It is also used for ion selective electrodes. TFPB is known as Kobayashi’s reagent.
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3. Y. Takahashi, et al., Facile and Highly Selective Synthesis of 2, 2-Dialkyl-1, 5-Lactones by the Calboxylation of Primary, Tertiary-1, 4-Diols with Formic Acid or Copper(I)Carbonyls in the Presence of Concentrated Sulfuric Acid. Chem Lett. 1982;11:1187-1188.
4. H. Iwamoto, et al., Anion-Catalyzed Phase-Transfer Catalysis. I. Application to Diazo-Coupling Reactions. Bull Chem Soc Jpn. 1983;56:796-801.
5. H. Iwamoto, et al., Diazotization of Pentafluoroaniline by Means of Anion-Catalyzed Phase Transfer Catalysis in a Hydrophobic Organic Solvent. J Fluor Chem. 1984;24:535-537.
6. H. Nishida, et al., Tetrakis[3, 5-bis(trifluoromethyl)phenyl]borate. Highly Lipophilic Stable Anionic Agent for Solvent-extraction of Cations. Bull Chem Soc Jpn. 1984;57:2600-2604.
7. Y. Shiraki, et al., Anion-Catalyzed Phase-Transfer Catalysis. II. Effects of Anionic Tetrakis[3, 5-Bis(Trifluoromethyl)Phenyl]Borate Catalyst in Phase-Transfer-Catalyzed Sulfonium Ylide Formation. Bull Chem Soc Jpn. 1985;58:3041-3042.
8. N. Ishibashi, et al., Vitamin B1-Sensitive Poly(vinyl chloride) Membrane Electrode Based on Hydrophobic Tetraphenylborate Cation Exchangers. Anal Sci. 1988;4:527-528.
9. G. H. Zhang, et al., Vitamin B1 sensitive poly(vinyl chloride) membrane electrode based on hydrophobic tetraphenylborate derivatives and their application. Anal Chem. 1990;62:1644-1648.
10. T. Nagamura, et al., Control of Molecular Orientation of 4, 4 EBipyridinium Cation Radicals in Novel Photochromic Monolayer Assemblies. J Chem Soc Chem Commun. 1990;9:703-704.
11. T. Nagamura, et al., Novel Photochromic Polymer Films Containing Ion-pair Charge-transfer Complexes of 4, 4 EBipyridinium Ions for Optical Recording. J Chem Soc Chem Commun. 1991;2:72-74.
12. M. Kira, et al., An NMR Study of the Formation of Silyloxonium Ions by Using Tetrakis[3, 5-Bis(Trifluoromethyl)Phenyl]Borate as Counteranion. J Am Chem Soc. 1992;114:6697-6700.