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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

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

signalword

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 Germany

WGK 3

Flash Point F

1.4 °F - closed cup

Flash Point C

-17 °C - closed cup

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How should Product 216143, Tetrabutylammonium fluoride solution be stored?

    This product is hygroscopic and should be stored under inert gas, such as nitrogen, and at 2-8 deg C, which is in accordance with our MSDS.

  4. What applications can 216143 Tetrabutylammonium fluoride solution, be used in?

    This product can be used as a fluorinating reagent.

  5. What causes Product 216143, Tetrabutylammonium fluoride solution, to turn purple?

    Our specifications for this product indicate the material should be colorless to yellow in color. Contact with ketones will immediate discoloration sometimes appearing purple in color. 

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
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)
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)
Fabio Galeotti et al.
Journal of chromatography. A, 1284, 141-147 (2013-03-05)
In this study, by using tetrabutylammonium bisulfate as ion-pairing reagent, we were able to separate all the main heparin/heparan sulfate disaccharides generated by the action of heparinases along with the main Hep tetrasaccharide possessing a 3-O-sulfate group on the sulfoglucosamine...

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