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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

Codice CAS
429-41-4
Sinonimi
TBAF

Dimensioni Prezzo ($) Quantità Disponibilità
25ml 32,30
100ml 59,40
500ml 192,00
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Tetra-n-butylammonium fluoride, 1M soln. in THF

MDL
MFCD00011747
EINECS
207-057-2

Proprietà chimiche

Formula
C16H36FN
Peso formula
261.47
Punto di infiammabilità
-17°(1°F)
Densità
0.903
Sensibilità
Hygroscopic
Solubilità
Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H302-H333-H314-H318-H351-H335

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

Dichiarazioni precauzionali: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3570522
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2923.90
TSCA
Yes

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