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368-39-8 - Triethyloxonium tetrafluoroborate, 95%, stab. with 3-5% diethyl ether - A14420 - Alfa Aesar

A14420 Triethyloxonium tetrafluoroborate, 95%, stab. with 3-5% diethyl ether

CAS Number

Size Price ($) Quantity Availability
25g 77.20
100g 235.00
500g 887.00
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Triethyloxonium tetrafluoroborate, 95%, stab. with 3-5% diethyl ether


Chemical Properties

Formula Weight
Melting point
Moisture Sensitive
Soluble in dichloromethane.


Triethyloxonium tetrafluoroborate is used as a powerful alkylating agent, especially for ethylation. It is used for the modification of carboxyl residues in proteins. It is involved in the preparation of µ -amino esters from lactams.


Moisture sensitive and hygroscopic. Store in a cool place. Incompatible with strong oxidizing agents.

Literature References

Trialkyloxonium salts, also known as Meerwein's salts, are powerful alkylating agents: Chem. Ber., 89, 209, 2060 (1956). For a brief feature on uses of Meerwein's salts in synthesis, see: Synlett, 195 (2004).

In combination with a hindered base, e.g. N-Ethyl­diisopropyl­amine, A11801, is a convenient reagent for the conversion of carboxylic acids to their ethyl esters by O-alkylation: Tetrahedron Lett., 4741 (1971); Org. Synth. Coll., 6, 576 (1988).

Secondary and tertiary amides are O-alkylated to give immonium salts and imino ethers, respectively. Reduction with borohydride provides an effective amide to amine conversion: Tetrahedron Lett., 61 (1968):

Likewise, N-alkylation of nitriles results in their activation to reduction by triethylsilane to give aldehydes, via the imines: Synthesis, 420 (1973); J. Chem. Soc., Chem. Commun., 45 (1974); J. Org. Chem., 46, 602 (1981).

For further reactions of trialkyloxonium salts, see Trimethyl­oxonium tetrafluoroborate, A15175.

Landman, M.; Levell, T. J.; Conradie, M. M.; van Rooyen, P. H.; Conradie, J. Structural and conformational study of pentacarbonyl and phosphine substituted Fischer alkoxy-and aminocarbene complexes of molybdenum. J. Mol. Struct. 2015, 1086, 190-200.

Ammazzini, S.; Onor, M.; Pagliano, E.; Mester, Z.; Campanella, B.; Pitzalis, E.; Bramantia, D.; Ulivo, A. Determination of thiocyanate in saliva by headspace gas chromatography-mass spectrometry, followg a single-step aqueous derivatization with triethyloxonium tetrafluoroborate. J. Chromatogr. A 2015, 1400, 124-130.

GHS Hazard and Precautionary Statements

Hazard Statements: H228-H314-H318

Flammable solid. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
Packing Group
Harmonized Tariff Code


  • A10173

    Trifluoromethanesulfonic acid, 98+%
  • A15175

    Trimethyloxonium tetrafluoroborate, 96%
  • A15806

    Nitrosonium tetrafluoroborate, 98%
  • A16625

    Potassium carbonate, anhydrous, 99%
  • A18766

    N,N-Dimethylbenzamide, 98+%

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