ChemicalBook Product Catalog Surfactant Caionic surfactants Quaternary Ammonium type Tetrabutylammonium Fluoride

Tetrabutylammonium Fluoride

Product NameTetrabutylammonium Fluoride
CAS429-41-4
MFC16H36FN
MW261.46
EINECS207-057-2
MOL File429-41-4.mol

Chemical Properties

Melting point	62-63 °C(lit.)
Density	0.953 g/mL at 25 °C
refractive index	n20/D 1.456
Flash point	1 °F
storage temp.	2-8°C
solubility	Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.
form	Solution
color	Clear light greenish to brown
Water Solubility	Insoluble in water.
Sensitive	Hygroscopic
Merck	14,9187
BRN	3570522
Exposure limits	ACGIH: TWA 2.5 mg/m3 NIOSH: IDLH 250 mg/m3
InChI	1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
InChIKey	FPGGTKZVZWFYPV-UHFFFAOYSA-M
SMILES	[F-].CCCC[N+](CCCC)(CCCC)CCCC
CAS DataBase Reference	429-41-4(CAS DataBase Reference)
EPA Substance Registry System	1-Butanaminium, N,N,N-tributyl-, fluoride (429-41-4)

Safety Information

Hazard Codes	C,F,Xi
Risk Statements	34-19-11-36/37/38-40-37
Safety Statements	26-27-36/37/39-45-33-29-16-36
RIDADR	UN 3261 8/PG 2
WGK Germany	3
F	3
Hazard Note	Flammable/Irritant
TSCA	TSCA listed
HazardClass	3
PackingGroup	II
HS Code	29239000
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Chronic 3 Eye Irrit. 2 Repr. 2 Skin Irrit. 2

MSDS

Provider	Language
TBAF	English
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Clear light greenish to amber or brown solution

Uses

Catalyst for etherification of alcohols and phenols with alkyl halides Catalyst for benzylation reactions.

Uses

Tetrabutylammonium fluoride is a reagent in organic syntheses in addition, condensation, base-catalyzed cyclization reactions, fluorination and desulfonylation reactions and as a deprotecting agent. Typically dried prior to use.

Uses

Tetrabutylammonium fluoride (TBAF) is a commonly used organic soluble fluoride salt. It is used as a base, a phase transfer catalyst, and as a fluoride source. In the research field of fluoride sensor development, TBAF is used as an easy to handle and measurable fluoride anion source. The fluoride in TBAF, once dissolved, can be thought of as a free fluoride with little interaction with the ammonium cation. Since TBAF should not absorb light at wavelengths greater than 240nm, it is useful to monitor sensing reactions with visible spectroscopy.

Definition

ChEBI: Tetrabutylammonium fluoride is a fluoride salt and a tetrabutylammonium salt. It has a role as a phase-transfer catalyst.

Synthesis

392-56-3

10442-39-4

1217-44-3

429-41-4

Synthesis of TBAF; Anhydrous tetrabutylammonium fluoride (TBAF):; 0.67 g of tetrabutylammonium cyanide (TBACN) was dissolved in 2.5 ml of tetrahydrofuran (THF) and the resulting solution was cooled to -65 °C. In a separate vessel, 0.3 mL of hexafluorobenzene (C6F6) was dissolved in 0.5 mL of THF and cooled to -65°C. The hexafluorobenzene solution was slowly added to the cooled TBACN solution and the mixture was gradually warmed (over 4 hours) to -15°C. During the reaction, the solution changed from colorless to yellow-green and precipitated a white solid. The mixture was cooled again to -65 °C, the solid was collected by filtration and washed twice with cold THF. All separation operations need to be carried out below -36°C. The resulting white or light yellow TBAF solid can be stored in a refrigerator at -36°C for a short period of time. If the reaction mixture is used directly, the overall yield of TBAF exceeds 95% (based on TBACN, as verified by burst experiments with benzyl chloride). Isolated yields of the solid product ranged from 40% to 70%, depending on the efficiency of the washing and filtration steps.1H NMR ((CD3)2SO) δ 3.23 (8H, m), 1.56 (8H, m), 1.28 (8H, sextuple peak, J = 7.31 Hz), 0.86 (12H, t, J = 7.31 Hz); 19F NMR ((CD3)2SO) δ -72.6 ppm(s); 13C NMR ((CD3)2SO) δ 57.5, 23.1, 19.2, 13.5 ppm.

References

[1] Patent: US2006/89514, 2006, A1. Location in patent: Page/Page column 5

Preparation Products And Raw materials