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90520

Sigma-Aldrich

Triethyloxonium tetrafluoroborate

≥97.0% (T)

Synonym(s):

Et3OBF4, Meerwein′s reagent, Triethyloxonium fluoroborate

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About This Item

Linear Formula:
(C2H5)3O(BF4)
CAS Number:
368-39-8
Molecular Weight:
189.99
Beilstein/REAXYS Number:
3598090
MDL number:
MFCD00044423
UNSPSC Code:
12352001
PubChem Substance ID:
329769918
NACRES:
NA.22

Quality Level

100

assay

≥97.0% (T)

form

crystals

contains

1-3% ether as stabilizer

solubility

methylene chloride: 20 mg/mL, clear, colorless

functional group

ether

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CC[O+](CC)CC

InChI

1S/C6H15O.BF4/c1-4-7(5-2)6-3;2-1(3,4)5/h4-6H2,1-3H3;/q+1;-1

InChI key

IYDQMLLDOVRSJJ-UHFFFAOYSA-N

Application

Triethyloxonium 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.

Other Notes

Powerful ethylating agent; Esterification of acids; Modifies carboxyl residues in proteins

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH014 - EUH019

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8841
BCCB6987
BCBS4750V
BCBF3940V
BCBL7522V

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Synthesis of substituted imidazolines via [3+ 2]-cycloaddition of aziridines with nitriles
Prasad BAB, et al.
Tetrahedron Letters, 45(6), 1137-1141 (2004)
N-Alkylation of N-arylsulfonyl-α-amino acid methyl esters by trialkyloxonium tetrafluoroborates
De Marco R, et al.
Tetrahedron, 67(50), 9708-9714 (2011)
H. Meerwein et al.
Angewandte Chemie (International Edition in English), 72, 927-927 (1960)
A mild and facile route to ω-amino esters
Menezes, R and Smith, MB
Synthetic Communications, 18(14), 1625-1636 (1988)
The nature of amino acid side chains which are critical for the activity of lysozyme.
S M Parsons et al.
Biochemistry, 8(2), 700-712 (1969-02-01)
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