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90520

Sigma-Aldrich

Triethyloxonium tetrafluoroborate

≥97.0% (T)

Synonym(s):

Et3OBF4, Meerwein′s reagent, Triethyloxonium fluoroborate

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$151.00
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25 G
$151.00
100 G
$408.00

About This Item

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

$151.00


Available to ship onApril 29, 2025Details


Request a Bulk Order

Quality Level

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.[1]
  • In the preparation of substituted imidazolines from aziridines and nitriles via [3+2]-cycloaddition reaction.[2]
  • 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.[3]

Other Notes

Powerful ethylating agent[4][5]; Esterification of acids[6]; Modifies carboxyl residues in proteins[7][8]

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

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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The identification of aspartic acid residue 52 as being critical to lysozyme activity.
S M Parsons et al.
Biochemistry, 8(10), 4199-4205 (1969-10-01)
D.J. Raber et al.
The Journal of Organic Chemistry, 44, 1149-1149 (1979)
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)
A mild and facile route to ω-amino esters
Menezes, R and Smith, MB
Synthetic Communications, 18(14), 1625-1636 (1988)
M.J. Diem et al.
The Journal of Organic Chemistry, 42, 1801-1801 (1977)

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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