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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

Quality Level

200

Assay

95%

form

solid

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.

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

Certificates of Analysis (COA)

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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)
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
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
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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