692360

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

• Synonym(s): Benzene, 1,3-bis(trifluoromethyl)-, boron complex, NaBARF, Tetrakis[3,5-bis(trifluoromethyl)phenyl]boron sodium
• Empirical Formula (Hill Notation): C₃₂H₁₂BF₂₄Na
• CAS Number: 79060-88-1
• Molecular Weight: 886.20
• Beilstein: 5474788
• MDL number: MFCD00043323
• UNSPSC Code: 12161600
• PubChem Substance ID: 329761488
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• reaction suitability: core: sodium; reagent type: catalyst
• SMILES string: [Na+].FC(F)(F)c1cc(cc(c1)C(F)(F)F)[B-](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)(c3cc(cc(c3)C(F)(F)F)C(F)(F)F)c4cc(cc(c4)C(F)(F)F)C(F)(F)F
• InChI: 1S/C32H12BF24.Na/c34-25(35,36)13-1-14(26(37,38)39)6-21(5-13)33(22-7-15(27(40,41)42)2-16(8-22)28(43,44)45,23-9-17(29(46,47)48)3-18(10-23)30(49,50)51)24-11-19(31(52,53)54)4-20(12-24)32(55,56)57;/h1-12H;/q-1;+1
• InChI key: LTGMONZOZHXAHO-UHFFFAOYSA-N

Description

General description

Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, also known as NaBArF, is widely used as a catalyst in the cyclopolymerization of functionalized trienes. NaBArF also acts as a precursor to synthesize other tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB)-based reagents.Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, also known as NaBAr′4, is a stable and highly soluble compound that has been used as a source of the [BArF] counterion in chemical synthesis. It has been found to be resistant to degradation by various oxidants and highly lipophilic. This compound has been used as a convenient reagent for the generation and stabilization of cationic electrophilic metal alkyl complexes. It has also been used in the living polymerization of ethylene, oligomerization of α-olefins, and olefin hydrogenation and hydrosilylation.

Application

The TFPB anion can be used to catalyze:

• In-situ diazo-coupling and N- and C-nitrosations.
• Synthesis of oxirane from different carbonyl substrates and trimethylsulfonium chloride via phase-transfer catalysis.
• Synthesis of ion selective membranes⁹

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable