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

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

CAS: 368-39-8 | C6H15BF4O | 189.99 g/mol
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100 g
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500 g
Catalog number ALF-A14420-22
HSN 29209099
Price (INR)
23,590.00
Each
Quantity:
100 g
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Price (INR)
23,590.00
Each
Chemical Identifiers
CAS368-39-8
IUPAC Nametetrafluoroboranuide; triethyloxidanium
Molecular FormulaC6H15BF4O
InChI KeyIYDQMLLDOVRSJJ-UHFFFAOYSA-N
SMILESF[B-](F)(F)F.CC[O+](CC)CC
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SpecificationsSpecification SheetSpecification Sheet
FormCrystals or Crystalline powder
Appearance (Color)White to cream
Assay (Aqueous acid-base Titration)>94.0 to <106.0%
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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
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.

Solubility
Soluble in dichloromethane.

Notes
Moisture sensitive and hygroscopic. Store in a cool place. Incompatible with strong oxidizing agents.
RUO – Research Use Only

General References:

  1. 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).
  2. In combination with a hindered base, e.g. N-Ethyl diisopropyl amine, 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).
  3. 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):
  4. 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).
  5. For further reactions of trialkyloxonium salts, see Trimethyl oxonium tetrafluoroborate, A15175.
  6. 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.
  7. 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.