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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
Pricing and availability is not currently available.

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

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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.[1] NaBArF also acts as a precursor to synthesize other tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB)-based reagents.[2][3]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.[4]
  • Synthesis of oxirane from different carbonyl substrates and trimethylsulfonium chloride via phase-transfer catalysis.[5]
  • Synthesis of ion selective membranes[6]9

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
MKCX1045
MKCV2699
MKCR8284
MKCQ6262
MKCP6934

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Double cyclopolymerization of functionalized trienes catalyzed by palladium complexes
Motokuni K, et al.
Macromolecules, 44, 751-756 (2011)
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)
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)
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)
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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