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216143

Sigma-Aldrich

Tetrabutylammonium fluoride solution

1.0 M in THF

Synonym(s):
TBAF solution
Linear Formula:
[CH3(CH2)3]4NF
CAS Number:
Molecular Weight:
261.46
Beilstein:
3762762
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

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.

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

Packaging

5 mL in glass bottle
1 L in Sure/Seal™
50, 100, 4×100, 500 mL in Sure/Seal™
2.5 L in glass bottle

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificate of Analysis

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Certificate of Origin

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Articles

Introduction of Terminal Azide and Alkyne Functionalities in Polymers

Click chemistry, and the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in particular, is a powerful new synthetic tool in polymer chemistry and material science.

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