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429-41-4 - Tetra-n-butylammonium fluoride, 1M soln. in THF - TBAF - A10588 - Alfa Aesar

A10588 Tetra-n-butylammonium fluoride, 1M soln. in THF

CAS-Nummer
429-41-4
Synonyme
TBAF

Größe Preis ($) Menge Verfügbarkeit
25ml 28,80
100ml 54,37
500ml 167,40
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Tetra-n-butylammonium fluoride, 1M soln. in THF

MDL
MFCD00011747
EINECS
207-057-2

Chemische Eigenschaften

Formel
C16H36FN
Molmasse
261.47
Flammpunkt
-17°(1°F)
Dichte
0.903
Sensitivität
Hygroscopic
Löslichkeit
Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.

Anwendungen

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.

Bemerkungen

Store in a cool place. Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents and oxygen.

Literaturverweise

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.

Specific reagent for the cleavage of silyl ethers, including TBDMS: J. Am. Chem. Soc., 94, 6190 (1972), (see tert-Butyl­dimethyl­chlorosilane, 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-Butyl­diphenyl­chlorosilane, A12721 and Chlorotriisopropyl­silane, A17376).

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 (trimethyl­silyl)­acetate, A17707): J. Am. Chem. Soc., 98, 2346 (1976); Org. Synth. Coll., 7, 512 (1990):

For the cleavage of disilanes to give "metal-free" silyl anions, see Hexamethyl­disilane, A13155.

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.

Reagent for deprotection of N-Boc groups under mild conditions: Tetrahedron Lett., 43, 589 (2002).

Many other examples exist where the reagent acts as a base in organic synthesis:

Acylation of hindered OH groups: Tetrahedron Lett., 1691 (1977). Nitro-aldol formation from aldehydes and nitro compounds (Henry reaction) facilitated by high pressure: Angew. Chem. Int. Ed., 23, 617 (1984). Dieckmann-type cyclization of a diester: Org. Synth. Coll., 8, 71 (1993). Catalyzes the regioselective N-alkylation of silylated purines with chloromethyl ethers: Helv. Chim. Acta, 72, 1495 (1989).

For nucleophilic displacement of halide or tosylate by TBAF in the preparation of alkyl and acyl fluorides, see: J. Org. Chem., 49, 3216 (1984); Org. Synth. Coll., 8, 258 (1993).

Reviews:

Fluoride ion as a base in organic synthesis: Chem. Rev., 80, 429 (1980). Synthetic aspects of the use of organosilicon compounds under nucleophilic catalysis conditions: Tetrahedron, 44, 2675 (1988). For a brief feature on uses of TBAF, see: Synlett, 2125 (2002).

Zhang, F.; Wu, X.; Wang, L.; Liu, H.; Zhao, Y. General and efficient one-pot synthesis of novel sugar/heterocyclic (aryl) 1, 2-diketones from sugar terminal alkynes by Sonogashira/tetra-n-butylammonium permanganate oxidation. Carbohydr. Res. 2015, 417 41-51.

Parr, B. T.; Economou, C.; Herzon, S. B. A concise synthesis of (+)-batzelladine B from simple pyrrole-based starting materials. Nature 2015, 525 (7570), 507-510.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H225-H314-H351-H302-H335

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Suspected of causing cancer. Harmful if swallowed. May cause respiratory irritation.

Sicherheitshinweise: P210-P260-P201-P261-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
3570522
Gefahrenklasse
3
Verpackungsgruppe
II
Harmonized Tariff Code
2923.90
TSCA
Yes

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