86872
Tetrabutylammonium fluoride trihydrate
≥97.0% (NT)
Synonym(s):
TBAF
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About This Item
Linear Formula:
[CH3(CH2)3]4NF · 3H2O
CAS Number:
Molecular Weight:
315.51
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-057-2
Beilstein/REAXYS Number:
3761900
MDL number:
Assay:
≥97.0% (NT)
Form:
crystals
Quality Level
assay
≥97.0% (NT)
form
crystals
mp
62-63 °C (lit.)
functional group
amine
SMILES string
O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC
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
InChI key
VEPTXBCIDSFGBF-UHFFFAOYSA-M
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.
Application
Tetrabutylammonium fluoride trihydrate can be used as a base:
It can be used to catalyze ethynylation of quinolines and isoquinolines using calcium carbide in aqueous N,N-dimethylacetamide.
- 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.
Reactant for:
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions
Preparation of deprotecting agents in preparation of cellulose derivatives
Synthesis of lipophilic peptides for DNA transfections in vivo
Dehydrobromination reactions
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
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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
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Find documentation for the products that you have recently purchased in 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)
T.W. Greene et al.
Protective Groups in Organic Synthesis (1991)
Tetrabutylammonium fluoride-induced dehydrobromination of vinyl bromides to terminal acetylenes
Okutani M and Mori Y
Tetrahedron Letters, 48(39), 6856-6859 (2007)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 86872-250G | 04061833042007 |
| 86872-50G | 04061833042014 |
| 86872-10G | 04061833041994 |