Product codeT037 TFPB
Chemical nameTetrakis[3,5-bis(trifluoromethyl)phenyl]borate, sodium salt
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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.
1) H. Kobayashi, T. Sonoda, H. Iwamoto and M. Yoshimura, "Tetrakis[3,5-di(F-methyl) phenyl] borate as the First Efficient Negatively Charged Phase Transfer Catalyst. Kinetic Evidences", Chem. Lett., 1981, 579.
2) H. Kobayashi, T. Sonoda and H. Iwamoto, "The First Application of Anion-catalyzed Phase-transfer Catalysis to Friedel-Crafts Alkylation", Chem. Lett., 1982, 1185.
3) Y. Takahashi, N. Yoneda and H. Nagai, "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, 1187.
4) H. Iwamoto, M. Yoshimura, T. Sonoda and H. Kobayashi, "Anion-Catalyzed Phase-Transfer Catalysis. I. Application to Diazo-Coupling Reactions", Bull. Chem. Soc. Jpn.,1983, 56, 796.
5) H. Iwamoto, T. Sonoda and H. Kobayashi, "Diazotization of Pentafluoroaniline by Means of Anion-Catalyzed Phase Transfer Catalysis in a Hydrophobic Organic Solvent", J. Fluorine Chem., 1984, 24, 535.
6) H. Nishida, N. Takada, M. Yoshimura, T. Sonoda and H. Kobayashi, "Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Highly Lipophilic Stable Anionic Agent for Solvent-extraction of Cations", Bull. Chem. Soc. Jpn., 1984, 57, 2600.
7) Y. Shiraki, K. Onitsuka, K. Takuma, T. Sonoda and H. Kobayashi, "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.
8) N. Ishibashi, T. Imato, G. H. Zhang, Y. Asano, T. Sonoda and H. Kobayashi, "Vitamin B1-Sensitive Poly(vinyl chloride) Membrane Electrode Based on Hydrophobic Tetraphenylborate Cation Exchangers", Anal. Sci., 1988, 4, 527.
9) G. H. Zhang, T. Imato, Y. Asano, T. Sonoda, H. Kobayashi and N. Ishibashi, "Vitamin B1-Sensitive Poly(vinyl chloride) Membrane Electrode Based on Hydrophobic Tetraphenylborate Derivatives and Their Application", Anal. Chem., 1990, 62, 1644.
10) T. Nagamura, Y. Isoda, K. Sakai and T. Ogawa, "Control of Molecular Orientation of 4,4'-Bipyridinium Cation Radicals in Novel Photochromic Monolayer Assemblies", J. Chem. Soc. Chem. Commun., 1990, 703.
11) T. Nagamura and Y. Isoda, "Novel Photochromic Polymer Films Containing Ion-pair Charge-transfer Complexes of 4,4'-Bipyridinium Ions for Optical Recording", J. Chem. Soc. Chem. Commun., 1991, 72.
12) M. Kira, T. Hino and H. Sakurai, "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.
Handling and storage condition
|Appearance：||White crystalline powder|
|Purity (Absorbance)：||≧ 99.0 % (as anhydrous)|
|Solubility in diethyl ether：||To pass test (clear, colorless)|