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

CAS: 368-39-8 MDL: MFCD00044423  EINECS: 206-705-1
UN#:UN2925Hazard Class:4.1Packing Group:II

 

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Chemical Properties

Formula: C6H15BF4O  Melting point: 84-89°
Formula weight: 189.99  Sensitivity: Moisture Sensitive

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.


Other References

Beilstein: 3598090
UN#: UN2925
Harmonized Tariff Code:   2920.90

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-P280-P303+P361+P353-P305+P351+P338-P310

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. 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. Immediately call a POISON CENTER or doctor/physician.

FlammableCorrosive

Risk & Safety

Risk Phrases: 11-34
Flammable. Causes burns.
Safety Phrases: 16-26-36/37/39-45
Keep away from sources of ignition - No Smoking. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Corrosive Highly Flammable
TSCA: Yes
RTECS: RR4584700