TFPB

- Overview
  - 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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- Properties
  - Categories
    
    Ion Analysis
    
    Alternative Name
    
    Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, sodium salt, dihydrate
    
    CAS Number
    
    79060-88-1
    
    Molecular Formula
    
    C32H12BF24Na
    
    Molecular Weight
    
    886.2
    
    Appearance
    
    White crystalline powder
    
    Purity
    
    ≥99.0% (Titration, as anhydrous))
    
    Storage
    
    ambient temperature
    
    Shipping
    
    ambient temperature
    
    * For research use only
- Applications
  - Application
    
    Anion excluder
- Reference
  - 1) H. Kobayashi, et al., Tetrakis[3, 5-di(F-methyl) phenyl] borate as the First Efficient Negatively Charged Phase Transfer Catalyst. Kinetic Evidences. Chem Lett. 1981;10:579-580.
    
    2) H. Kobayashi, et al., The First Application of Anion-catalyzed Phase-transfer Catalysis to Friedel-Crafts Alkylation. Chem Lett. 1982;11:1185-1186.
    
    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.

MSDS

TFPB

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