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692360

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ6262
MKCP6934
MKCM9938
MKCL7909
MKCF5233

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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)
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)
Enantioselective hydrogenation of acyclic aromatic N-aryl imines catalyzed by an iridium complex of (S, S)-1, 2-bis (tert-butylmethylphosphino) ethane.
Imamoto T, et al.
Organic Letters, 8(11), 2289-2292 (2006)
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)
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)
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