Triethyloxonium tetrafluoroborate

Triethyloxonium tetrafluoroborate
  • CAS No.:368-39-8
Other grades of this product :
Triethyloxonium tetrafluoroborate Basic information
Product Name:Triethyloxonium tetrafluoroborate
Synonyms:TRIETHYLOX;Oxonium,triethyl-,tetrafluoroborate;Triethyloxonium Tetrafluoroborate Discontinued;Triethyloxonium tetrafluoroborate, 1M solution in methylene chloride, AcroSeal;(15% in DichloroMethane, ca. 1Mol/L) [Ethylating Reagent];TriethyloxoniuM Tetrafluoroborate triethyloxonium tetrafluoroborate(1-);MEERWEIN'S REAGENT
CAS:368-39-8
MF:C6H15BF4O
MW:189.99
EINECS:206-705-1
Product Categories:B (Classes of Boron Compounds);Iodonium Sulfonium & Oxonium Compounds;Oxonium Compounds;Tetrafluoroborates;Alkyl Transfer;C-X Bond Formation (Non-Halogen);Organic-metal salt;API intermediates;Wittig Reagents;Synthetic Reagents
Mol File:368-39-8.mol
Triethyloxonium tetrafluoroborate Chemical Properties
Melting point 96-97°C
density 1.328 g/mL at 25 °C
storage temp. 2-8°C
solubility methylene chloride: 20 mg/mL, clear, colorless
form Powder
color White
Water Solubility REACTS
Sensitive Moisture Sensitive
Merck 14,5796
BRN 3598090
Exposure limitsACGIH: TWA 50 ppmOSHA: TWA 25 ppm; STEL 125 ppmNIOSH: IDLH 2300 ppm
InChIKeyIYDQMLLDOVRSJJ-UHFFFAOYSA-N
CAS DataBase Reference368-39-8(CAS DataBase Reference)
EPA Substance Registry SystemOxonium, triethyl-, tetrafluoroborate(1-) (368-39-8)
Safety Information
Hazard Codes C
Risk Statements 34-40-14-67-37
Safety Statements 23-24/25-26-36/37/39-45-22
RIDADR UN 3265 8/PG 2
WGK Germany 2
RTECS RR4584700
3-10-16-21
Hazard Note Corrosive
TSCA Yes
HazardClass 4.1
PackingGroup II
HS Code 29420000
Toxicitydnd-smc 500 mmol/L CPBTAL 23,2485,75
MSDS Information
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Triethyloxonium tetrafluoroborate English
SigmaAldrich English
ACROS English
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Triethyloxonium tetrafluoroborate Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder.
UsesTriethyloxonium tetrafluoroborate is used as a powerful alkylating agent, especially for ethylation. It is used for the modification of carboxyl residues in proteins. It is involved in the preparation of μ-amino esters from lactams. It is also alkylating agent for nucleophilic functional groups in organic synthesis.
ApplicationTriethyloxonium tetrafluoroborate can be used:To prepare amino esters by reacting with lactams followed by hydrolysis.In the preparation of substituted imidazolines from aziridines and nitriles via [3+2]-cycloaddition reaction.For the N-alkylation of a series of N-arylsulfonyl-α-amino acid methyl esters having variable substituents at 4th position of the sulfonamide aromatic ring.Synthesis of HDET2.
Safety ProfileTriethyloxonium tetrafluoroborate is a powerful ethylating agent, although the hazards are diminished because it is non-volatile. It releases strong acid upon contact with water. When heated to decomposition it emits toxic vapors of boronand Fí. Mutation data reported.
SynthesisTriethyloxonium tetrafluoroborate is prepared from boron trifluoride,diethyl ether and epichlorohydrin:4 Et2O·BF3+ 2 Et2O + 3 C2H3(O)CH2Cl → 3 Et3O+BF4+ B[(OCH(CH2Cl)CH2OEt]3The trimethyloxonium salt is available from dimethyl ether via an analogous route.These salts do not have long shelf-lives at room temperature. They degrade by hydrolysis:[(CH3CH2)3O]+BF4+ H2O → (CH3CH2)2O + CH3CH2OH +HBF4
Purification MethodsCrystallise it from diethyl ether. It is very hygroscopic, and must be handled in a dry box and stored at 0o. [Meerwein Org Synth Coll Vol V 1096 1973.] Pure material should give a clear and colourless solution in dichloromethane (1 in 50, w/v). [Beilstein 1 IV 1322.]

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