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420-37-1 - Trimethyloxonium tetrafluoroborate, 96% - A15175 - Alfa Aesar

A15175 Trimethyloxonium tetrafluoroborate, 96%

Codice CAS
420-37-1
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
10g 56,50
50g 254,00
250g 1106,00
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Trimethyloxonium tetrafluoroborate, 96%

MDL
MFCD00011798
EINECS
206-994-4

Proprietà chimiche

Formula
C3H9BF4O
Peso formula
147.91
Punto di fusione
ca 190° dec.
Sensibilità
Moisture Sensitive
Solubilità
Soluble in nitrobenzene, nitromethane, chloroform, hot acetone, liquid sulfur dioxide. Slightly soluble in dichloromethane. Insoluble in common organic solvents.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

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. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3597303
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2920.90
TSCA
Yes

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