tetrabutylazanium fluoride

• ChemBase ID: 94540
• Molecular Formular: C16H36FN
• Molecular Mass: 261.4621432
• Monoisotopic Mass: 261.28317838
• SMILES: [N+](CCCC)(CCCC)(CCCC)CCCC.[F-]
• Canonical SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[F-]
• 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
• InChIKey: FPGGTKZVZWFYPV-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium fluoride
• IUPAC Traditional name: tetrabutylammonium ion fluoride; tetrabutylammonium fluoride
• Synonyms: Tetrabutylammonium fluoride on silica gel; Tetrabutylammonium fluoride on alumina; Tetra-n-butylammonium fluoride, 1M soln. in THF; Tetra-n-butylammonium fluoride trihydrate; TBAF; Tetrakis(but-1-yl)ammonium fluoride 1.0M solution in THF; TBAF solution; Tetrabutylammonium fluoride solution; Tetra-n-butylammonium fluoride; Tetra-n-butylammonium fluoride; Tetrabutylammonium fluoride; 硅胶负载四丁基氟化铵; 氧化铝负载四丁基氟化铵; 四正丁基氟化铵, 1M THF溶液; 四正丁基氟化铵三水合物; TBAF 溶液; 四丁基氟化铵 溶液; 四正丁基氟化铵

Database IDs

• CAS Number: 429-41-4; 87749-50-6
• EC Number: 207-057-2
• MDL Number: MFCD00011747; MFCD00149981
• Beilstein Number: 3570522; 3762762; 3761900
• PubChem SID: 24862218; 162081194; 24852802; 24860012; 24861982
• PubChem CID: 2724141
• CHEMBL: 1078233
• Chemspider ID: 2006300
• Wikipedia Title: Tetra-n-butylammonium_fluoride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.3234289
• LogD (pH = 7.4): 1.3234289
• Log P: 1.3234289
• Molar Refractivity: 91.3961 cm^3
• Polarizability: 31.734425 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-60°C; 58-60 °C (trihydrate)
• Boiling Point: 65-67°C
• Flash Point: 1.4 °F; -17 °C; -17°C; -17°C(1°F)
• Density: 0.903; 0.903 g/mL at 25 °C; 0.953 g/mL at 25 °C
• Refractive Index: n20/D 1.456

Safety Information

• Storage Warning: Highly Flammable/Corrosive/Harmful/Irritant/Hygroscopic/Keep Cold/Store under Argon; Hygroscopic
• European Hazard Symbols: Corrosive (C); Flammable (F); Toxic (T); X
• UN Number: 1759; 1760; 2924; UN2811; UN2922; UN2924
• German water hazard class: 3
• Hazard Class: 3; 6.1; 8
• Packing Group: 1; 2; II
• Risk Statements: 11-19-22-34; 11-19-34-37; 25-34; 25-38-41; 34
• Safety Statements: 16-26-36/37/39-45; 20-23-26-36/37/39-45; 26-27-36/37/39-45; 26-36/37/39-45; 9-16-26-33-36/37/39-45-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H335; H225-H314-H351-H302-H335; H300-H314-H318; H300-H315-H318; H314
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310; P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1759 8/PG 1; UN 1759 8/PG 2; UN 1760 8/PG 2; UN 2924 3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: 75% w/w aq. soln.; 95+%; 98%
• Concentration: ~1 M in THF; ~75% in H2O (NT); 1.0 M in THF; 1M soln. in THF; 75 wt. % in H2O
• Grade: purum
• Impurities: ~5 wt. % water; 4-5% water
• Extent of Labeling: 15 wt. % loading
• Capacity: ~1.5 mmol/g (F-)
• Linear Formula: (CH3CH2CH2CH2)4N(F); [CH3(CH2)3]4NF

DETAILS

Sigma Aldrich - 331953

Packaging
25 g in poly bottle
Application

• Catalyst for etherification of alcohols and phenols with alkyl halides1
• Catalyst for benzylation reactions2

Sigma Aldrich - 358673

Packaging
5, 25 g in poly bottle

Sigma Aldrich - 361399

Packaging
100, 500 g in poly bottle
25 g in amber poly
Application
Reactant for preparation of:
• Triple monoamine reuptake inhibitors as a new generation of antidepressants1
• Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions2
• Oligoribonucleotides with phosphonate-modified linkages3
• Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride4
• Conjugated dienoic acid esters using Suzuki coupling reactions5
• Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity6
• Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors7
• Anti-diabetic polyacetylenic glucosides8

Sigma Aldrich - 86923

Application
Reactant for preparation of:
• Triple monoamine reuptake inhibitors as a new generation of antidepressants1
• Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions2
• Oligoribonucleotides with phosphonate-modified linkages3
• Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride4
• Conjugated dienoic acid esters using Suzuki coupling reactions5
• Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity6
• Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors7
• Anti-diabetic polyacetylenic glucosides8

Sigma Aldrich - 86900

Application
Reactant for preparation of:
• Triple monoamine reuptake inhibitors as a new generation of antidepressants1
• Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions2
• Oligoribonucleotides with phosphonate-modified linkages3
• Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride4
• Conjugated dienoic acid esters using Suzuki coupling reactions5
• Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity6
• Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors7
• Anti-diabetic polyacetylenic glucosides8

Sigma Aldrich - 216143

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Packaging
1 L in Sure/Seal™
5 mL in glass bottle
2, 2.5 L in glass bottle
50, 100, 500 mL in Sure/Seal™
Application
Reactant for preparation of:
• Triple monoamine reuptake inhibitors as a new generation of antidepressants1
• Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions2
• Oligoribonucleotides with phosphonate-modified linkages3
• Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride4
• Conjugated dienoic acid esters using Suzuki coupling reactions5
• Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity6
• Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors7
• Anti-diabetic polyacetylenic glucosides8

REFERENCES

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