Skip to Content
Merck

86872

Tetrabutylammonium fluoride trihydrate

≥97.0% (NT)

Synonym(s):

TBAF

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Linear Formula:
[CH3(CH2)3]4NF · 3H2O
CAS Number:
87749-50-6
Molecular Weight:
315.51
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
57653206
EC Number:
207-057-2
Beilstein/REAXYS Number:
3761900
MDL number:
MFCD00149981

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Tetrabutylammonium fluoride trihydrate, ≥97.0% (NT)

InChI key

VEPTXBCIDSFGBF-UHFFFAOYSA-M

InChI

1S/C16H36N.FH.3H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;;;/h5-16H2,1-4H3;1H;3*1H2/q+1;;;;/p-1

SMILES string

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

assay

≥97.0% (NT)

form

crystals

mp

62-63 °C (lit.)

functional group

amine

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

Reactant for:
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions
Tetrabutylammonium fluoride trihydrate can be used as a base:
  • For the dehydrobromination of vinyl bromides to terminal acetylenes.
  • In the conversion of 1,1-dibromo-1-alkenes to terminal alkynes via Corey–Fuchs reaction.
  • In Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryltrialkoxysilanes in the presence of a palladium catalyst.

It can be used to catalyze ethynylation of quinolines and isoquinolines using calcium carbide in aqueous N,N-dimethylacetamide.

General description

Tetrabutylammonium fluoride trihydrate is a mild base used in reactions like aldol-type condensation reactions, Michael-type reactions, ring-opening reactions. Its is also used as a promoter in cross-coupling reactions and cyclization of carbocycles and heterocycles.

Other Notes

Reagent for the cleavage of silyl ethers and other silyl protecting groups; Catalyst for various reactions with silicon compounds; Use as a base in organic synthesis; Instability of anhydrous TBAF

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM8210
BCCL3110
BCCK2214
BCCJ7325
BCCF9682

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

An Efficient Method for the Production of Terminal Alkynes from 1, 1-Dibromo-1-alkenes and its Application in the Total Synthesis of Natural Product Dihydroxerulin
Liu S, et al.
advanced synthesis and catalysis, 357(2-3), 553-560 (2015)
Tetrabutylammonium fluoride-induced dehydrobromination of vinyl bromides to terminal acetylenes
Okutani M and Mori Y
Tetrahedron Letters, 48(39), 6856-6859 (2007)
T.W. Greene et al.
Protective Groups in Organic Synthesis (1991)
D. Albanese et al.
Synthesis, 34-34 (1994)
J.H. Clark
Chemical Reviews, 80, 429-429 (1980)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service