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Sigma-Aldrich

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

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About This Item

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

form

powder

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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A facile in-situ diazo-coupling reactions under two-phase conditions catalyzed by tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate ion.
Iwamoto H, et al.
Tetrahedron Letters, 24(43), 4703-4706 (1983)
[(3, 5-(CF3) 2C6H3) 4B]-[H (OEt2) 2]+: a convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes.
Brookhart M, et al.
Organometallics, 11(11), 3920-3922 (1992)
Double cyclopolymerization of functionalized trienes catalyzed by palladium complexes
Motokuni K, et al.
Macromolecules, 44, 751-756 (2011)
Synthesis and Structure of the Thallium (I) Salt of the Tetrakis {3, 5-bis (trifluoromethyl) phenyl} borate Anion.
Hughes R P, et al.
Inorganic Chemistry, 36(8), 1726-1727 (1997)
Alina M Schimpf et al.
Journal of the American Chemical Society, 137(1), 518-524 (2014-12-10)
Plasmonic doped semiconductor nanocrystals promise exciting opportunities for new technologies, but basic features of the relationships between their structures, compositions, electronic structures, and optical properties remain poorly understood. Here, we report a quantitative assessment of the impact of composition on
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