Substance
ID:714340
Names and Identifiers
IUPAC name
tetrabutylazanium fluoride
Synonyms
TBAFTetra-n-butylammonium fluoride, 1M soln. in THF四正丁基氟化铵, 1M THF溶液
IUPAC Traditional name
tetrabutylammonium fluoride
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Properties
Safety Information
Hazard Class
3
Packing Group
II
GHS Pictograms
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Respiratory sensitization, category 1
Germ cell mutagenicity, categories 1A,1B,2
Carcinogenicity, categories 1A,1B,2
Reproductive toxicity, categories 1A,1B,2
Specific Target Organ Toxicity – Single exposure, categories 1,2
Specific Target Organ Toxicity – Repeated exposure, categories 1,2
Aspiration Hazard, category 1
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
GHS Hazard statements
H225-H314-H351-H302-H335
European Hazard Symbols
Harmful (X)
Flammable (F)
Corrosive (C)TSCA Listed
是
UN Number
UN2924
Safety Statements
9-16-26-33-36/37/39-45-60
GHS Precautionary statements
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
Risk Statements
11-19-22-34
Storage Warning
Hygroscopic
Product Information
Concentration
1M soln. in THF
Physical Property
Flash Point
-17°C(1°F)
Density
0.903
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Reagent for deprotection of N-Boc groups under mild conditions: Tetrahedron Lett., 43, 589 (2002).
• 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).
• 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.
• 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).
• 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):
• 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.
• For the cleavage of disilanes to give "metal-free" silyl anions, see Hexamethyldisilane, A13155.
• Many other examples exist where the reagent acts as a base in organic synthesis:
• 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).
• Reviews:
• 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).