Tetramethylammonium fluoride

Base Information

• Chemical Name: Tetramethylammonium fluoride
• CAS No.: 373-68-2
• Molecular Formula: C4H12FN
• Molecular Weight: 93.1444
• Hs Code.: 29239000
• European Community (EC) Number: 206-769-0
• DSSTox Substance ID: DTXSID40883374
• Wikipedia: Tetramethylammonium_fluoride
• Wikidata: Q56292058
• Mol file: 373-68-2.mol

Synonyms:tetraamethylammonium acetate;tetramethylammonium;tetramethylammonium bromide;tetramethylammonium chloride;tetramethylammonium fluoride;tetramethylammonium hydrogen dichloride;tetramethylammonium hydroxide;tetramethylammonium hydroxide pentahydrate;tetramethylammonium iodide;tetramethylammonium nitrate;tetramethylammonium perchlorate;tetramethylammonium sulfate (2:1);tetramethylammonium tribromide;tetramethylammonium triiodide;trimethylaminomethane

Chemical Property of Tetramethylammonium fluoride

Chemical Property:

• Appearance/Colour: Solid.
• Melting Point: 170 °C
• PSA: 0.00000
• LogP: -2.67360
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 93.095377549
• Heavy Atom Count: 6
• Complexity: 19.1

Purity/Quality:

99% ^*data from raw suppliers

Tetramethylammonium fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+](C)(C)C.[F-]
• 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: 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. 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)

Technology Process of Tetramethylammonium fluoride

There total 9 articles about Tetramethylammonium fluoride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.3%

carbonic acid dimethyl ester (616-38-6) → tetramethylammonium fluoride (373-68-2)

Guidance literature:

With ammonium fluoride; at 169.84 ℃; for 8h;

DOI:10.1039/b601343k

Reference yield:

[NMe4][XeO(fluoride)3] (1239907-95-9) → xenon difluoride (13709-36-9) + tetramethylammonium fluoride (373-68-2)

Guidance literature:

In neat (no solvent, solid phase); byproducts: O2, [N(CH3)4][XeO2F3]; (anhydrous conditions); warming Xe compd. to 25°C; not isolated, Raman spectroscopy;

DOI:10.1021/ja103730c

Reference yield:

[NMe4][XeO(fluoride)3] (1239907-95-9) + sulfur dioxide (7446-09-5,12143-17-8,89125-89-3) → xenon difluoride (13709-36-9) + sulfur trioxide (7446-11-9) + tetramethylammonium fluoride (373-68-2)

Guidance literature:

In neat (no solvent); (anhydrous conditions); condensation of SO2 to Xe compd. at -196°C, warming to -78°C; not isolated;

DOI:10.1021/ja103730c

upstream raw materials:

tetramethlyammonium chloride

tetramethyl ammoniumhydroxide

tetramethylammonium hydrogen difluoride

carbonic acid dimethyl ester

Downstream raw materials:

Methyl fluoride

heptafluoro-isobutyric acid

perfluoro-2-methylpent-2-ene

trimethylsilyl fluoride

Refernces

• 1、 Breitenstein, Christoph,Ignat'ev, Nikolai,Frank, Walter. "Convenient synthesis of aliphatic (CF3)2N-compounds". . p. 166 - 177. Retrieved 2018.
• 2、 -. "METHOD FOR PREPARING TETRAMETHYLAMMONIUM FLUORIDE". Page/Page column 7. . Retrieved 2018/03/09.