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429-41-4 molecular structure
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tetrabutylazanium fluoride

ChemBase ID: 94540
Molecular Formular: C16H36FN
Molecular Mass: 261.4621432
Monoisotopic Mass: 261.28317838
SMILES and InChIs

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

Cite this record

CBID:94540 http://www.chembase.cn/molecule-94540.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
tetrabutylazanium fluoride
IUPAC Traditional name
tetrabutylammonium fluoride
tetrabutylammonium ion fluoride
Synonyms
TBAF
Tetrakis(but-1-yl)ammonium fluoride 1.0M solution in THF
Tetra-n-butylammonium fluoride
Tetrabutylammonium fluoride on alumina
Tetrabutylammonium fluoride on silica gel
TBAF solution
Tetrabutylammonium fluoride solution
Tetra-n-butylammonium fluoride trihydrate
Tetrabutylammonium fluoride
Tetra-n-butylammonium fluoride, 1M soln. in THF
Tetra-n-butylammonium fluoride
氧化铝负载四丁基氟化铵
硅胶负载四丁基氟化铵
TBAF 溶液
四正丁基氟化铵三水合物
四丁基氟化铵 溶液
四正丁基氟化铵
四正丁基氟化铵, 1M THF溶液
CAS Number
429-41-4
87749-50-6
EC Number
207-057-2
MDL Number
MFCD00011747
MFCD00149981
Beilstein Number
3761900
3570522
3762762
PubChem SID
24852802
24862218
162081194
24860012
24861982
PubChem CID
2724141
CHEMBL
1078233
Chemspider ID
2006300
Wikipedia Title
Tetra-n-butylammonium_fluoride

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.3234289  LogD (pH = 7.4) 1.3234289 
Log P 1.3234289  Molar Refractivity 91.3961 cm3
Polarizability 31.734425 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds 12  Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
54-60°C expand Show data source
58-60 °C (trihydrate) expand Show data source
Boiling Point
65-67°C expand Show data source
Flash Point
1.4 °F expand Show data source
-17 °C expand Show data source
-17°C expand Show data source
-17°C(1°F) expand Show data source
Density
0.903 expand Show data source
0.903 g/mL at 25 °C expand Show data source
0.953 g/mL at 25 °C expand Show data source
Refractive Index
n20/D 1.456 expand Show data source
Storage Warning
Highly Flammable/Corrosive/Harmful/Irritant/Hygroscopic/Keep Cold/Store under Argon expand Show data source
Hygroscopic expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
X expand Show data source
UN Number
1759 expand Show data source
1760 expand Show data source
2924 expand Show data source
UN2811 expand Show data source
UN2922 expand Show data source
UN2924 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
3 expand Show data source
6.1 expand Show data source
8 expand Show data source
Packing Group
1 expand Show data source
2 expand Show data source
II expand Show data source
Risk Statements
11-19-22-34 expand Show data source
11-19-34-37 expand Show data source
25-34 expand Show data source
25-38-41 expand Show data source
34 expand Show data source
Safety Statements
16-26-36/37/39-45 expand Show data source
20-23-26-36/37/39-45 expand Show data source
26-27-36/37/39-45 expand Show data source
26-36/37/39-45 expand Show data source
9-16-26-33-36/37/39-45-60 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS05 expand Show data source
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H314-H335 expand Show data source
H225-H314-H351-H302-H335 expand Show data source
H300-H314-H318 expand Show data source
H300-H315-H318 expand Show data source
H314 expand Show data source
GHS Precautionary statements
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
P210-P261-P280-P305 + P351 + P338-P310 expand Show data source
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
P280-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand Show data source
P280-P305 + P351 + P338-P310 expand Show data source
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 expand Show data source
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1759 8/PG 1 expand Show data source
UN 1759 8/PG 2 expand Show data source
UN 1760 8/PG 2 expand Show data source
UN 2924 3/PG 2 expand Show data source
Supplemental Hazard Statements
May form explosive peroxides. expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
75% w/w aq. soln. expand Show data source
95+% expand Show data source
98% expand Show data source
Concentration
~1 M in THF expand Show data source
~75% in H2O (NT) expand Show data source
1.0 M in THF expand Show data source
1M soln. in THF expand Show data source
75 wt. % in H2O expand Show data source
Grade
purum expand Show data source
Impurities
~5 wt. % water expand Show data source
4-5% water expand Show data source
Extent of Labeling
15 wt. % loading expand Show data source
Capacity
~1.5 mmol/g (F-) expand Show data source
Linear Formula
(CH3CH2CH2CH2)4N(F) expand Show data source
[CH3(CH2)3]4NF expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
Sigma Aldrich - 331953 external link
Packaging
25 g in poly bottle
Application

• Catalyst for etherification of alcohols and phenols with alkyl halides1
• Catalyst for benzylation reactions2
Sigma Aldrich - 358673 external link
Packaging
5, 25 g in poly bottle
Sigma Aldrich - 361399 external link
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 external link
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 external link
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
Sigma Aldrich - 86900 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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:
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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