Tetra-n-butylammonium fluoride, 1M soln. in THF, Thermo Scientific Chemicals
Tetra-n-butylammonium fluoride, 1M soln. in THF, Thermo Scientific Chemicals
Thermo Scientific Chemicals

Tetra-n-butylammonium fluoride, 1M soln. in THF, Thermo Scientific Chemicals

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Catalog number A10588.AC
also known as A10588-AC
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Price (USD)/ Each
43.65
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Save 4.95 (10%)
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Tetra-n-butylammonium fluoride, 1M soln. in THF, Thermo Scientific Chemicals
Catalog numberA10588.AC
Price (USD)/ Each
43.65
Online exclusive
48.60 
Save 4.95 (10%)
-
Add to cart
Chemical Identifiers
CAS429-41-4
IUPAC Nametetrabutylazanium fluoride
Molecular FormulaC16H36FN
InChI KeyFPGGTKZVZWFYPV-UHFFFAOYSA-M
SMILES[F-].CCCC[N+](CCCC)(CCCC)CCCC
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)Clear colorless to brown
Water Content (Karl Fischer Titration)<5.0%
FormLiquid
Assay (Non-aqueous acid-base Titration)0.95 - 1.10M
Assay (Titration ex Bromide)<1.0% Bromide impurity
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Tetra-n-butylammonium fluoride, 1M soln. in THF is used as a reactant for the preparation of triple monoamine reuptake inhibitors as a new generation of antidepressants, oligoribonucleotides with phosphonate-modified linkages, conjugated dienoic acid esters using Suzuki coupling reactions and polyacetylenic glucosides. It plays an important role in aryl alkyl alcohols through Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride. It is also used as a catalyst for the silylation reactions. In addition, it is used as a source of fluoride ion in organic solvents as well as for the deprotection of silyl ether groups.

Solubility
Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.

Notes
Store in a cool place. Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents and oxygen.
WARNING: Cancer – www.P65Warnings.ca.gov
RUO – Research Use Only

General References:

  1. Mild catalyst for the silylation of OH by silazanes: Tetrahedron Lett., 35, 8409 (1994), or by hydrosilanes and disilanes: Tetrahedron Lett., 35, 8413 (1994). See Appendix 4.
  2. Specific reagent for the cleavage of silyl ethers, including TBDMS: J. Am. Chem. Soc., 94, 6190 (1972), (see tert-Butyl dimethyl chlorosilane, A13064), as well as the more stable TBDPS: Org. Synth. Coll., 9, 4 (1998), and TIPS: J. Org. Chem., 45, 4797 (1980); (see also tert-Butyl diphenyl chlorosilane, A12721 and Chlorotriisopropyl silane, A17376).
  3. Ester enolates can be displaced from silicon, and trapped by reaction with carbonyl compounds without ɑ-hydrogens: Tetrahedron Lett., 1699 (1976). Under similar conditions, ketones with ɑ-hydrogens are converted under kinetic control to their silyl enol ethers with high (Z)-stereoselectivity (see Ethyl (trimethyl silyl) acetate, A17707): J. Am. Chem. Soc., 98, 2346 (1976); Org. Synth. Coll., 7, 512 (1990):
  4. For the cleavage of disilanes to give metal-free silyl anions, see Hexamethyl disilane, A13155.
  5. Promotes the directed aldol condensation of silyl enol ethers with aldehydes at low temperatures under very mild conditions: J. Org. Chem., 48, 932 (1983); alkali metal fluorides give poor results.
  6. Reagent for deprotection of N-Boc groups under mild conditions: Tetrahedron Lett., 43, 589 (2002).
  7. Many other examples exist where the reagent acts as a base in organic synthesis: