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Merck

216143

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:
Molecular Weight:
261.46
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3762762
Form:
liquid
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form

liquid

Quality Level

reaction suitability

core: ammonium

concentration

1.0 M in THF

impurities

~5 wt. % water

density

0.903 g/mL at 25 °C

functional group

amine

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

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.



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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

supp_hazards

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 1 petroleums + Hazardous rank II + Water insoluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

216143-20L:4.548173250861E12 + 216143-500ML:4.548173117034E12 + 216143-2.5L:4.54817311701E12 + 216143-100ML:4.548173117003E12 + 216143-1L:4.54817334274E12 + 216143-5ML:4.548173117041E12 + 216143-2L:4.548173117027E12 + 216143-50ML:4.548173332901E12

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Articles

クリックケミストリーのための高分子末端へのアジド基とアルキン基の導入について、具体例を示しています。

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.


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)
Chao Zhong et al.
Carbohydrate polymers, 94(1), 38-45 (2013-04-03)
In this article, a novel and high efficient solvent, tetra-n-Butylammonium Hydroxide (TBAH), was used for dissolution and isolation of straw cellulose from wheat straw. The composition analysis with gas chromatography (GC) and the spectroscopic characterization analysis conducted by X-Ray diffraction