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A15175 Trimethyloxonium tetrafluoroborate, 96%

CAS Number
420-37-1
Synonyms

Stock No. Size Price ($) Quantity Availability
A15175-09 10g 59.30
A15175-18 50g 264.00
A15175-30 250g 1162.00
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Trimethyloxonium tetrafluoroborate, 96%

MDL
MFCD00011798
EINECS
206-994-4

Chemical Properties

Formula
C3H9BF4O
Formula Weight
147.91
Melting point
ca 190° dec.
Storage & Sensitivity
Store at -20°C. Moisture Sensitive. Store under Nitrogen.
Solubility
Soluble in nitrobenzene, nitromethane, chloroform, hot acetone, liquid sulfur dioxide. Slightly soluble in dichloromethane. Insoluble in common organic solvents.

Applications

Trimethyloxonium tetrafluoroborate act as a avmethylating agent and activates C-X multiple bonds. It is involved in the esterification of polyfunctional carboxylic acids. It acts as a catalyst in the polymerization of cyclic sulfides and ethers. Further, it is used in Beckmann rearrangement of oximes.

Notes

Hygroscopic. Moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents and bases.

Literature References

Trialkyloxonium salts, also known as Meerwein's salts, are powerful alkylating agents under mild conditions. For general reactions of trialkyloxonium salts, see Triethyl­oxonium tetrafluoroborate, A14420 . For a brief feature of their uses in synthesis, see: Synlett, 195 (2004).

Alkylation of ethylene thioacetals proceeds only to the monoalkyl salt unless water is added, when the thioacetal is cleaved to give the carbonyl compound and the tetraalkyl ethane bis-sulfonium salt: Synthesis, 135 (1981). Alkylation on S to promote leaving group ability has also been used in a synthesis of oxiranes from ß-hydroxy sulfides: J. Am. Chem. Soc., 95, 3429 (1973); J. Chem. Soc., Chem. Commun., 714 (1975).

N,N-Dialkyl arylcarboxamides, useful as substrates for directed metallation reactions, can be converted to methyl esters in high yield: Tetrahedron, 56, 9875 (2000).

Nortcliffe, A.; Moody, C. J. Seven-membered ring scaffolds for drug discovery: Access to functionalised azepanes and oxepanes through diazocarbonyl chemistry. Bioorg. Med. Chem. 2015, 23 (11), 2730-2735.

Lim, J. Y.; Cunningham, M. J.; Davis, J. J.; Beer, P. D. Halogen bonding-enhanced electrochemical halide anion sensing by redox-active ferrocene receptors. Chem. Commun. 2015, 51 (78), 14640-14643.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H335

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

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
3597303
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2920.90
TSCA
Yes

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