Tetra-n-butylammonium fluoride

Tetra-n-butylammonium fluoride

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Names
IUPAC name Tetra-n-butylammonium fluoride
Identifiers
CAS Number	429-41-4 Y 87749-50-6 (trihydrate) N
ChEMBL	ChEMBL1078233 Y
ChemSpider	2006300 Y
Jmol 3D model	Interactive image
PubChem	2724141
InChI 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 Y Key: FPGGTKZVZWFYPV-UHFFFAOYSA-M Y InChI=1/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 Key: FPGGTKZVZWFYPV-REWHXWOFAO
SMILES [F-].CCCC[N+](CCCC)(CCCC)CCCC
Properties
Chemical formula	(C4H9)4NF
Molar mass	261.46 g/mol
Melting point	58 to 60 °C (136 to 140 °F; 331 to 333 K) (trihydrate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Tetra-n-butylammonium fluoride, commonly abbreviated to TBAF and n-Bu₄NF, is a quaternary ammonium salt with the chemical formula (CH₃CH₂CH₂CH₂)₄N⁺F⁻. It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents.

Preparation and properties

Because fluoride is such a strong hydrogen bond acceptor, its salts tend to be hydrated and of limited solubility in organic solvents. TBAF solves this problem, although the nature of the fluoride is uncertain because TBAF samples are almost always hydrated, resulting in the formation of bifluoride (HF₂⁻) hydroxide (OH⁻) as well as fluoride. Many applications tolerate heterogeneous or ill-defined fluoride sources.

Preparing anhydrous samples is of interest as the basicity of fluoride increases by more than 20 pK units on passing from aqueous to aprotic solvent. Many attempts have been made to produce anhydrous TBAF. Heating samples of the hydrated material to 77 °C under vacuum causes decomposition to the hydrogen difluoride salt. Similarly, samples dried at 40 °C under high vacuum still contain 10-30 mol% of water and some 10% of difluoride.

Anhydrous tetra-n-butylammonium fluoride has been prepared by the reaction of hexafluorobenzene and tetrabutylammonium cyanide. Solutions of the salt in acetonitrile and dimethyl sulfoxide are stable.

Reactions

As a source of fluoride ion in organic solvents, TBAF is used to remove silyl ether protecting groups. It is also used as a phase transfer catalyst and as a mild base. As a deprotecting group, TBAF in DMSO will convert O-silylated enolates into carbonyls. With C-Si bonds, TBAF gives carbanions that can be trapped with electrophiles or undergo protonolysis.

Further reading

• .

• Hui-Yin Li, Haoran Sun, Stephen G. DiMagno "Tetrabutylammonium Fluoride" e-EROS Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley doi:10.1002/9780470842898.rt015.pub2
• Nina Gommermann and Paul Knochel "N,N-Dibenzyl-N-[1-cyclohexyl-3-(trimethylsilyl)-2-propynyl]-amine from Cyclohexanecarbaldehyde, Trimethylsilylacetylene and Dibenzylamine" Org. Synth. 2007, 84, 1. doi:10.15227/orgsyn.084.0001