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216143

Sigma-Aldrich

Tetrabutylammonium fluoride solution

1.0 M in THF

Synonym(s):

TBAF solution

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About This Item

Linear Formula:
[CH3(CH2)3]4NF
CAS Number:
429-41-4
Molecular Weight:
261.46
Beilstein:
3762762
MDL number:
MFCD00011747
UNSPSC Code:
12352116
PubChem Substance ID:
24852802
NACRES:
NA.22

form

liquid

Quality Level

200

concentration

1.0 M in THF

impurities

~5 wt. % water

density

0.903 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

[F-].CCCC[N+](CCCC)(CCCC)CCCC

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

InChI key

FPGGTKZVZWFYPV-UHFFFAOYSA-M

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Application

Reactant for preparation of:
  • Triple monoamine reuptake inhibitors as a new generation of antidepressants
  • Alcohols via hydrolysis of alkyl silyl ethers neutral pH in mixed organic-aqueous buffered solutions
  • Oligoribonucleotides with phosphonate-modified linkages
  • Aryl alkyl alcohols via Nozaki-Hiyama allylation catalyzed by chiral bipyridyldiol ligands and chromium trichloride
  • Conjugated dienoic acid esters using Suzuki coupling reactions
  • Macrocyclic o-aminobenzamide Hsp90 inhibitorwith antitumor activity
  • Phospshoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors
  • Anti-diabetic polyacetylenic glucosides
Tetrabutylammonium fluoride (TBAF) can be used as a reagent:
  • For the deprotection of silyl and N-sulfonyl groups.
  • In the fluorination reactions.
  • To synthesize 2-substituted indoles by cyclization reaction of various 2-ethynylanilines with terminal alkynes using Pd catalyst. It can also be used as an activator in the synthesis of arylated or alkenylated alkynes by the coupling reaction of aryl and alkenyl halides with terminal alkynes in the presence of Pd catalyst.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019,EUH032

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificates of Analysis (COA)

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Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride
Yasuhara A, et al.
Journal of the Chemical Society. Perkin Transactions 1, 39(4), 529-534 (1999)
Non-Sonogashira-type palladium-catalyzed coupling reactions of terminal alkynes assisted by silver (I) oxide or tetrabutylammonium fluoride.
Mori A, et al.
Organic Letters, 2(19), 2935-2937 (2000)
Tetrabutylammonium Fluoride
Li Hui-Yin, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Deprotection of N-sulfonyl nitrogen-heteroaromatics with tetrabutylammonium fluoride
Yasuhara A and Sakamoto T
Tetrahedron Letters, 39(7), 595-596 (1998)
Erbo Shi et al.
Organic letters, 14(13), 3384-3387 (2012-06-27)
A metal-free C-H oxidation for the construction of allylic esters has been developed. The use of a commercially available and inexpensive catalyst and oxidant, and readily available starting materials, coupled with the operational simplicity of the reaction, renders the methodology
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