A14420

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

CAS Number 368-39-8

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

MDL: MFCD00044423
EINECS: 206-705-1

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.

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

Other References

Beilstein: 3598090
UN#: UN2925
Hazard Class: 4.1
Packing Group: II
Harmonized Tariff Code: 2920.90
TSCA: Yes
RTECS: RR4584700

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