Triethyloxonium tetrafluoroborate

• Catalog No.: A14420
• CAS Number: 368-39-8
• M. F.: C6H15BF4O
• M. W.: 189.9873128
• Purity: 95%, stab. with 3-5% diethyl ether

SYNONYMS

• Title: 三乙基氧鎓四氟硼酸盐
• IUPAC name: tetrafluoroboranuide; triethyloxidanium
• IUPAC Traditional name: triethyloxidanium tetrafluoroborate

DATABASE IDS

• CAS Number: 368-39-8
• Beilstein Number: 3598090
• EC Number: 206-705-1
• MDL Number: MFCD00044423

PROPERTIES

• Purity: 95%, stab. with 3-5% diethyl ether
• Melting Point: 84-89°C
• GHS Hazard statements: H228-H314-H318
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P280-P303+P361+P353-P305+P351+P338-P310
• Risk Statements: 11-34
• RTECS: RR4584700
• Safety Statements: 16-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 4.1
• UN Number: UN2925
• Packing Group: II

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.