373-68-2

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 NO: 373-68-2
• Molecular Formula: C₄H₁₂N*F
• Molecular Weight: 93.14
• EINECS: 206-769-0
• Product Categories: quarternary ammonium salts;Deprotecting Reagents;Fluoride Sources;Protection and Derivatization
• Mol File: 373-68-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 170°C (dec.)
• Appearance: /
• CAS DataBase Reference: Tetramethylammonium fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethylammonium fluoride(373-68-2)
• EPA Substance Registry System: Tetramethylammonium fluoride(373-68-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 373-68-2(Hazardous Substances Data)

Usage

Description

Tetramethylammonium 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.

Uses

Different sources of media describe the Uses of 373-68-2 differently. You can refer to the following data:
1. 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.
2. Reactant 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)

InChI:InChI=1/C4H12N.FH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

Upstream product

• 661-36-9 tetramethylammonium tetrafluoroborate 
• 1239907-95-9 [NMe₄][XeO(fluoride)3] 
• 7446-09-5 sulfur dioxide 
• 392-56-3 Hexafluorobenzene 
• 23237-02-7 tetramethylammonium cyanide 
• 616-38-6 carbonic acid dimethyl ester 
• 1643-35-2 tetramethylammonium hydrogen difluoride 
• 75-57-0 tetramethlyammonium chloride 
• 75-59-2 tetramethyl ammoniumhydroxide 

Downstream Products

• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 7727-37-9 nitrogen 
• 10102-43-9 nitrogen(II) oxide 
• 75-57-0 tetramethlyammonium chloride 
• 10024-97-2 dinitrogen monoxide 
• 7783-42-8 thionyl fluoride 
• 80764-08-5 tetramethylammonium bifluoride 
• 558-32-7 tetramethylammonium hexafluorophosphate 
• 328379-53-9 (pentafluorophenyl)fluoroxenon(II) 
• 144717-69-1 trans-[Pt(H)(F)(PCy₃)2] 
• 144717-67-9 trans-[Pt(H)(FHF)(PCy₃)2] 
• 17981-20-3 (α-Ethoxycarbonylmethyl-benzyloxy)-triethyl-zinn 
• 185250-10-6 Ir(H)2F(P(t)Bu₂Ph)2 

Relevant articles and documents

Hydrogen bonding. Part 66. Further studies of the fluoride ion assisted dissolution of 1-methyl-4,5-dicarboxyimidazole: Absence of cation participation and stoichiometric considerations

Excess 1-methyl-4,5-dicarboxyimidazole (H2MDCI) dissolves into saturated solution in the presence of sodium fluoride, and precisely four F are required for each H2MDCI solubilized. To account for the apparent removal of two acidic hydrogens from H2MDCI in the presence of undissociated diacid we postulated strong complexation of Na+ by MDCI2-. We now find that the dissolution behavior of H2MDCI in the presence of either cesium or tetramethylammonium fluoride is identical to that with sodium fluoride. As cesium ion should bind weakly if at all to MDCI2-, and tetramethylammonium ion should not be bound, we conclude that the cation present plays no role in the fluoride ion assisted dissolution of H2MDCI. Analysis of dissolution stoichiometry and titration data suggests the possibility that two F- react with H2MDCI to form HMDCI+ and HF2/- and that two more F are required but do not act to abstract acid hydrogen.

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

A fluoride salt ion liquid synthetic method of the

The invention relates to the field of organic chemical synthesis, particularly a synthesis method of a fluoride salt ionic liquid. The method comprises the following steps: adding excessive hydrofluoric acid, ammonium fluoride or ammonium bifluoride into halogenated imidazole and other raw materials, stirring in a closed environment, heating to 50-70 DEG C, and sufficiently reacting for at least 3 hours to obtain a non-dewatered fluoride salt ionic liquid; detecting, purifying and dewatering to obtain a thick liquid; and detecting the thick liquid to obtain the qualified fluoride salt ionic liquid. The method has the advantages of simple technique, no organic solvent, no waste and high end product purity.