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86872 Sigma-Aldrich

Tetrabutylammonium fluoride trihydrate

≥97.0% (NT)

Synonym: TBAF

  • CAS Number 87749-50-6

  • Linear Formula [CH3(CH2)3]4NF · 3H2O

  • Molecular Weight 315.51

  •  Beilstein/REAXYS Number 3761900

  •  EC Number 207-057-2

  •  MDL number MFCD00149981

  •  PubChem Substance ID 57653206

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Deprotecting Reagents, Fluoride Sources, Protection and Derivatization, Synthetic Reagents More...
Quality Level   200
assay   ≥97.0% (NT)
mp   62-63 °C (lit.)
storage temp.   room temp
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

Description

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

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.

Packaging

10, 50, 250 g in poly bottle

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
RIDADR 
UN 1759 8 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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