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281077

Sigma-Aldrich

Trimethyloxonium tetrafluoroborate

95%

Synonym(s):

Trimethyloxonium fluoroborate

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About This Item

Linear Formula:
(CH3)3O(BF4)
CAS Number:
420-37-1
Molecular Weight:
147.91
Beilstein:
3597303
EC Number:
206-994-4
MDL number:
MFCD00011798
UNSPSC Code:
12352107
PubChem Substance ID:
24856967
NACRES:
NA.22
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Quality Level

200

Assay

95%

form

solid

functional group

ether

storage temp.

−20°C

SMILES string

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

InChI

1S/C3H9O.BF4/c1-4(2)3;2-1(3,4)5/h1-3H3;/q+1;-1

InChI key

CZVZBKHWOFJNCR-UHFFFAOYSA-N

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General description

Trimethyloxonium tetrafluoroborate can be used as a methylating agent for the methylation of hydroxyl/carboxyl functional groups. It is capable of methylating polyfunctional carboxylic acids. It is also used as a catalyst for the polymerization of cyclic sulfides and ethers.

Application

Reagent for the methylation of hydroxyl groups recently used in a complex, multistep synthesis directed towards spirastrellolide, a marine natural product.[1]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4445
SHBR0502
SHBN5647
BCCF1809
BCCB5975

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Toward the total synthesis of spirastrellolide A. Part 2: Conquest of the northern hemisphere.
Alois Fürstner et al.
Angewandte Chemie (International ed. in English), 45(33), 5510-5515 (2006-08-15)
Marco Pacenti et al.
Biomedical chromatography : BMC, 22(10), 1155-1163 (2008-05-29)
A method for the determination of the organic acids directly in the urine employing derivatization with trimethyloxonium tetrafluoroborate as a methylating agent and sequential extraction by head space and direct immersion/solid phase microextraction is reported. Furoic acid, hippuric acid, methylhippuric
H M Liebich et al.
Journal of chromatography. A, 843(1-2), 237-245 (1999-07-10)
Trimethyloxonium tetrafluoroborate (TMO) is applied as derivatising reagent to transform urinary organic acids into their methyl esters. The method is suggested as an alternative to the use of diazomethane which is carcinogenic and explosive. In contrast to other methods avoiding
S Chericoni et al.
Journal of analytical toxicology, 35(4), 193-198 (2011-04-26)
The present work describes the validation of a novel aqueous in situ derivatization procedure with trimethyloxonium tetrafluoroborate (TMO) as methylating agent for the simultaneous, quantitative analysis of Δ(9)-tetrahydrocannabinol (THC) and 11-nor-Δ(9)-tetrahydrocannabinol carboxylic acid (THC-COOH) in human urine. The derivatizing agent
H M Liebich et al.
Journal of chromatography. B, Biomedical sciences and applications, 713(2), 427-432 (1998-09-24)
We developed a new sample preparation method for profiling organic acids in urine by GC or GC-MS. The method includes derivatisation of the organic acids directly in the aqueous urine using trimethyloxonium tetrafluoroborate as a methylating agent, extraction of the
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Questions

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  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

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  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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