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

CAS Number
368-39-8
Synonyms

Stock No. Size Price ($) Quantity Availability
A14420-14 25g 81.80
A14420-22 100g 250.00
A14420-36 500g 941.00
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Triethyloxonium tetrafluoroborate, 95%, stab. with 3-5% diethyl ether

MDL
MFCD00044423
EINECS
206-705-1

Chemical Properties

Formula
C6H15BF4O
Formula Weight
189.99
Melting point
84-89°
Storage & Sensitivity
Store at -20°C. Moisture Sensitive. Store under Nitrogen.
Solubility
Soluble in dichloromethane.

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.

Notes

Moisture sensitive and hygroscopic. Store in freezer. 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: H314-H335-H336

Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness.

Precautionary Statements: P260-P264b-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3598090
Hazard Class
4.1
Packing Group
II
Harmonized Tariff Code
2942.00
TSCA
Yes
RTECS
RR4584700

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