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459135

Sigma-Aldrich

Tetramethylammonium fluoride

97%

Synonym(s):

TMAF

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$113.00
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$113.00

Estimated to ship onMay 09, 2025

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1 G
$113.00
5 G
$532.00

About This Item

Linear Formula:
(CH3)4NF
CAS Number:
373-68-2
Molecular Weight:
93.14
EC Number:
206-769-0
MDL number:
MFCD00011627
UNSPSC Code:
12352116
PubChem Substance ID:
24869514
NACRES:
NA.22

$113.00

Estimated to ship onMay 09, 2025

Request a Bulk Order

Quality Level

100

assay

97%

form

solid

mp

170 °C (dec.) (lit.)

functional group

amine

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.[1] It can react with aminosilanes to generate onium amide bases in situ, which can deprotonate heteroarenes.[2]
Useful for halogen exchange.

pictograms

Exclamation mark
GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
0000237393
0000237388
0000133007
0000215223
0000212254

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Nucleophilic deoxyfluorination of phenols via aryl Fluorosulfonate intermediates.
Schimler SD, et al.
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.
Inamoto K, et al.
Tetrahedron, 70(43), 7917-7922 (2014)
Martin-Louis Y Riu et al.
Science advances, 6(13), eaaz3168-eaaz3168 (2020-04-02)
This exploratory synthesis investigation was undertaken to determine the viability of replacing a single carbon vertex with another p-block element in a highly strained tetrahedrane molecule. Phosphorus was selected for this purpose because the stable molecular form of elemental phosphorus
Yasuyuki Ishida et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 27(10), 1053-1056 (2011-10-12)
Thermochemolysis-gas chromatography in the presence of tetramethylammonium acetate was applied to the direct determination of terephthalic acid (TPA) contained in solid decomposition products obtained from the hydrothermal recycling process of poly(ethylene terephthalate) (PET). On the chromatograms of the hydrothermal decomposition
Hui Chong et al.
Langmuir : the ACS journal of surfaces and colloids, 28(4), 2091-2098 (2011-11-08)
A new water-soluble conjugated polymer containing fluorene and boron-dipyrromethene repeat units in the backbones (PBF) that exhibits red emission was synthesized and characterized. Cationic PBF forms uniform nanoparticles with negatively charged disodium salt 3,3'-dithiodipropionic acid (SDPA) in aqueous solution through
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