Tetramethylammonium fluoride Chemical Properties

Melting point:

170 °C (dec.) (lit.)

storage temp. 

Store at room temperature

form 

solid

Appearance

White to off-white <39°C Solid,>42°C Liquid

InChI

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

InChIKey

HQFTZNVQVRRDLN-UHFFFAOYSA-M

SMILES

[N+](C)(C)(C)C.[F-]

CAS DataBase Reference

373-68-2(CAS DataBase Reference)

EPA Substance Registry System

Tetramethylammonium 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

• Language:English Provider:Tetramethylammonium fluoride

Tetramethylammonium fluoride Usage And Synthesis

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.

Uses

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(373-68-2)Related Product Information

• Tetramethylammonium fluoride tetrahydrate
• Octamethylcyclotetrasiloxane
• Methyl tetrahydrophthalic anhydride
• Tetramethylammonium hydroxide
• Tetramethylammonium hydroxide pentahydrate
• FLUORIDE STANDARD
• Tetrabutylammonium fluoride
• Ammonium fluoride
• N,N,N',N'-Tetramethylethylenediamine
• Tetramethylpyrazine
• Tetramethylammonium acetate
• Tetramethylammonium sulfate
• Hexamethylenetetramine
• Benzyltrimethylammonium fluoride
• TETRABUTYLAMMONIUM FLUORIDE
• Tetrapropyl Ammonium Fluoride
• Tetramethylammonium fluoride trihydrate
• TETRA-N-BUTYLAMMONIUM DIHYDROGENTRIFLUORIDE