Tetramethylammonium fluoride

Tetramethylammonium fluoride Basic information
Product Name:Tetramethylammonium fluoride
Synonyms:Tetramethylammonium Fluoridede;n,n,n-trimethyl-methanaminiufluoride;TETRAMETHYLAMMONIUM FLUORIDE;Tetramethylammoniumfluoride,20%AqueousSolution;Tetramethylammonium fluoride, anhydrous;Methanaminium, N,N,N-trimethyl-, fluoride;Tetramethylazanium fluoride;Tetramethylaminium·fluoride
CAS:373-68-2
MF:C4H12FN
MW:93.14
EINECS:206-769-0
Product Categories:Deprotecting Reagents;Fluoride Sources;Protection and Derivatization;quarternary ammonium salts
Mol File:373-68-2.mol
Tetramethylammonium fluoride Structure
Tetramethylammonium fluoride Chemical Properties
Melting point 170 °C (dec.) (lit.)
InChIKeyHQFTZNVQVRRDLN-UHFFFAOYSA-M
CAS DataBase Reference373-68-2(CAS DataBase Reference)
EPA Substance Registry SystemTetramethylammonium fluoride (373-68-2)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36
RIDADR 2811
WGK Germany 3
HazardClass 6.1(b)
PackingGroup III
HS Code 29239000
MSDS Information
ProviderLanguage
Tetramethylammonium fluorideEnglish
Tetramethylammonium fluoride Usage And Synthesis
DescriptionTetramethylammonium fluoride is the quaternary ammonium salt with the formula (CH3)4NF. This hygroscopic white solid is a source of “naked fluoride”, that is fluoride ions not connected to a metal atom in a complex. Most other soluble salts of fluoride are in fact bifluorides, HF2–. Historically, there has been two main approaches to prepare TMAF:
(i) Via neutralization of tetramethylammonium hydroxide (TMAOH) with HF.
(ii) through the metathesis reaction of different ammonium salts with inorganic sources of fluoride such as KF or CsF.
Due to the high basicity of the fluoride anion, the salt reacts slowly with acetonitrile, inducing its dimerization to CH3C(NH2)=CHCN, which co-crystallizes.
UsesTetramethylammonium 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.
UsesReactant for:
Halide-induced ring opening of 2-substituted aziridinium saltsSynthesis of fluoro aromatics via fluorodenitration reactionsSynthesis of sevoflurane in ionic liquids by halogen-exchange fluorinationSynthesis of fluorinated Poly(oxomolybdates)
Tetramethylammonium fluoride Preparation Products And Raw materials
Preparation Products1-Methylpyrrole-2-carbonitrile–>1-METHYLTRYPTAMINE–>Methanaminium, N,N,N-trimethyl-, azide–>Tetramethylammonium trifluoromethylselenate

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