Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

459135

Sigma-Aldrich

Tetramethylammonium fluoride

97%

Synonym(s):

TMAF

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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. It can react with aminosilanes to generate onium amide bases in situ, which can deprotonate heteroarenes.
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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000237388
0000237393
0000133007
0000215223
0000212254

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Nucleophilic deoxyfluorination of phenols via aryl Fluorosulfonate intermediates.
Schimler SD, et al.
Journal of the American Chemical Society, 139(4), 1452-1455 (2017)
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
Mei Fang et al.
Nanotechnology, 23(14), 145601-145601 (2012-03-22)
Magnetite nanoparticles have been prepared by co-precipitation using a custom-designed jet mixer to achieve rapid mixing (RM) of reactants in a timescale of milliseconds. The quick and stable nucleation obtained allows control of the particle size and size distribution via
Jalila Amorri et al.
Environmental science and pollution research international, 18(9), 1606-1616 (2011-05-25)
Complex organic compounds found in oil and sediments linked with a particular source (such as algae, bacteria or vascular plants) are defined as biomarkers and are useful dating indicators in organic geochemistry. This paper presents the composition of the organic
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service