Tetramethylammonium fluoride

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Tetramethylammonium fluoride
Names
IUPAC name
tetramethylazanium;fluoride
Identifiers
3D model (JSmol)
ChemSpider
EC Number 206-769-0
Properties
C4H12FN
Molar mass 93.145 g·mol−1
Appearance white solid
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362, P363, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetramethylammonium fluoride is the quaternary ammonium salt with the formula (CH3)4NF. This colorless 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. Tetramethylammonium fluoride is produced by combining tetramethylammonium hydroxide and hydrogen fluoride in isopropanol. 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.[1]

Related salts[edit]

(CH3)3P=CH2 + KHF2 → (CH3)4PF + KF
In the gas phase, tetramethylphosphonium fluoride exists as the phosphorane, but in acetonitrile solution, it dissociates into ions.[2]

References[edit]

  1. ^ Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R.; Feng, J. A. (1990). "Syntheses, Properties, and Structures of Anhydrous Tetramethylammonium Fluoride and Its 1:1 Adduct with trans-3-Amino-2-butenenitrile". Journal of the American Chemical Society. 112: 7619–7625. doi:10.1021/ja00177a025.CS1 maint: Uses authors parameter (link)
  2. ^ Kornath, Andreas; Neumann, F.; Oberhammer, H. (2003). "Tetramethylphosphonium Fluoride: "Naked" Fluoride and Phosphorane". Inorganic Chemistry. 42: 2894–2901. doi:10.1021/ic020663c.CS1 maint: Multiple names: authors list (link)
  3. ^ Schwesinger, Reinhard (2001). "1,1,1,3,3,3-Hexakis(dimethylamino)-1λ5,3λ5-diphosphazenium Fluoride". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–2. doi:10.1002/047084289X.rh014m.
  4. ^ Haoran Sun & Stephen G. DiMagno (2005). "Anhydrous Tetrabutylammonium Fluoride". Journal of the American Chemical Society. 127 (7): 2050–1. doi:10.1021/ja0440497. PMID 15713075.