459135
Tetramethylammonium fluoride
97%
Synonym(s):
TMAF
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About This Item
Linear Formula:
(CH3)4NF
CAS Number:
Molecular Weight:
93.14
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
mp
170 °C (dec.) (lit.)
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
Related Categories
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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 Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Konrad Rykaczewski et al.
Langmuir : the ACS journal of surfaces and colloids, 29(3), 881-891 (2012-12-25)
The prospect of enhancing the condensation rate by decreasing the maximum drop departure diameter significantly below the capillary length through spontaneous drop motion has generated significant interest in condensation on superhydrophobic surfaces (SHS). The mobile coalescence leading to spontaneous drop
Yusuke Ide et al.
Chemical communications (Cambridge, England), 48(56), 7073-7075 (2012-06-12)
Hiroshima University Silicate-1 (HUS-1), composed of silicate sheets with a halved sodalite cage and the interlayer tetramethylammonium (TMA) cation in the cage, was modified with dimethyldichlorosilane to form the organic derivative in which a dimethyl group was grafted onto the
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