86872

Tetrabutylammonium fluoride trihydrate

≥97.0% (NT)

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

Properties

• Quality Level: 200
• assay: ≥97.0% (NT)
• form: crystals
• mp: 62-63 °C (lit.)
• 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.

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 Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302,H315,H319,H361fd,H412
• pcodes: P202 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges