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Sigma-Aldrich

Tetrabutylammonium tetrafluoroborate

99%

Synonym(s):

Ammonium tetra-n-butyl tetrafluoroborate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(BF4)
CAS Number:
429-42-5
Molecular Weight:
329.27
Beilstein:
3577508
EC Number:
207-058-8
MDL number:
MFCD00011634
UNSPSC Code:
12352116
PubChem Substance ID:
24853042
NACRES:
NA.22
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Quality Level

200

Assay

99%

form

powder

mp

155-161 °C (lit.)

solubility

methanol: soluble 10%, clear, colorless

SMILES string

F[B-](F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.BF4/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2-1(3,4)5/h5-16H2,1-4H3;/q+1;-1

InChI key

NNZZSJSQYOFZAM-UHFFFAOYSA-N

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General description

Tetrabutylammonium tetrafluoroborate is used as an electrolyte for the series of arylketone synthesis.[1] [2]

Tetrabutylammonium tetrafluoroborate (TBATFB) is a phase transfer catalyst.[3] It can be synthesized by the reaction between 30% aqueous solution of tetrafluoroboric acid and 40% aqueous solution of tetrabutylamonium hydroxide.[4] Tetrabutylammonium tetrafluoroborate acts as an electrolyte and inhibits the self-assembly of alkylthiosulfate on gold.[5]

Application

Tetrabutylammonium tetrafluoroborate may be used in the following studies:
  • As supporting electrolyte in the voltammetric determination of Δ(9)-tetrahydrocannabinol (Δ(9)-THC).[6]
  • Synthesis of biologically relevant macrolactones, Sansalvamide A.[7]
  • As supporting electrolyte in the determination of the oxidation and reduction potentials of 5,10,15,20-tetra[3-(3-trifluoromethyl)phenoxy]porphyrin by cyclic voltammetry.[8]
  • Preparation of 1:1 adduct with 1,10-phenanthroline.[9]
  • Used to prepare other tetrabutylammonium salts in aqueous solutions.[10]
  • As electrolyte additive in the synthesis of conducting poly(thiophenes).[11]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV1430
BCCL0841
BCBL9106V
BCBM0012V
BCBB4702V

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Electropolymerization of thiophene with and without aniline in acetonitrile.
Can M, et al.
Turkish Journal of Chemistry, 22, 47-54 (1998)
An efficient electrochemical oxidation of C (sp3)-H bond for the synthesis of arylketones
kong, et al.
Molecular Catalysis, 530, 112633-112633 (2022)
N-Alkylation of imides using phase transfer catalysts under solvent-free conditions
Jakowska, et al.
Journal of Heterocyclic Chemistry, 45, 1371-1375 (2008)
N-Alkylation of imides using phase transfer catalysts under solvent-free conditions.
Jaskowska J and Kowalski P.
Journal of Heterocyclic Chemistry, 45(5), 1371-1375 (2008)
José Antonio Morales-Serna et al.
Organic & biomolecular chemistry, 8(21), 4940-4948 (2010-09-08)
A facile and mild macrolactonization reaction of ω-hydroxy acids was developed based on the transesterification of benzotriazole esters. Treatment of ω-hydroxy acids with 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) and 1-hydroxy benzotriazole (HOBT) in chloroform provided macrolactones in excellent yields. The reactions were
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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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