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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)
Gold nanoparticles solid contact for ion-selective electrodes of highly stable potential readings
Ewa Jaworska, Michal Wojcik, Anna Kisiel, Jozef Mieczkowski, Agata Michalska
Talanta, 85(4), 1986-1989 (2011)
Trityl tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate: a new hydride abstraction reagent.
Bahr S R and Boudjouk P
The Journal of Organic Chemistry, 57(20), 5545-5547 (1992)
Anion-catalyzed Phase-transfer Catalysis. II. Effects of Anionic Tetrakis [3, 5-bis (trifluoromethyl) phenyl] borate Catalyst in Phase-transfer-catalyzed Sulfonium Ylide Formation.
Shiraki Y, et al.
Bulletin of the Chemical Society of Japan, 58(10), 3041-3042 (1985)
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