459135
Tetramethylammonium fluoride
97%
Synonym(s):
TMAF
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About This Item
Recommended Products
Quality Level
assay
97%
form
solid
mp
170 °C (dec.) (lit.)
SMILES string
[F-].C[N+](C)(C)C
InChI
1S/C4H12N.FH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1
InChI key
GTDKXDWWMOMSFL-UHFFFAOYSA-M
Application
Reactant for:
- Halide-induced ring opening of 2-substituted aziridinium salts
- Synthesis of fluoro aromatics via fluorodenitration reactions
- Synthesis of sevoflurane in ionic liquids by halogen-exchange fluorination
- Synthesis of fluorinated Poly(oxomolybdates)
Tetramethylammonium fluoride may be used in combination with sulfuryl fluoride for the conversion of aryl phenols to aryl fluorides. It can react with aminosilanes to generate onium amide bases in situ, which can deprotonate heteroarenes.
Useful for halogen exchange.
signalword
Warning
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Nucleophilic deoxyfluorination of phenols via aryl Fluorosulfonate intermediates.
Journal of the American Chemical Society, 139(4), 1452-1455 (2017)
Use of tetramethylammonium fluoride (TMAF) and alkali metal alkoxides as an activator for catalytic deprotonative functionalization of heteroaromatic C (sp2)?H bonds.
Tetrahedron, 70(43), 7917-7922 (2014)
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