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Merck

281077

Trimethyloxonium tetrafluoroborate

95%

Synonym(s):

Trimethyloxonium fluoroborate

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About This Item

Linear Formula:
(CH3)3O(BF4)
CAS Number:
Molecular Weight:
147.91
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-994-4
Beilstein/REAXYS Number:
3597303
MDL number:

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Product Name

Trimethyloxonium tetrafluoroborate, 95%

form

solid

InChI key

CZVZBKHWOFJNCR-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

95%

functional group

ether

storage temp.

−20°C

Quality Level

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1 of 4

This Item
8.4163890520164577
assay

95%

assay

≥95.0% (acidimetric)

assay

≥97.0% (T)

assay

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

form

solid

form

crystals

form

crystals

form

solid

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

functional group

ether

functional group

-

functional group

ether

functional group

phenyl

Application

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

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.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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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
V M Mahnir et al.
Toxicon : official journal of the International Society on Toxinology, 28(11), 1255-1263 (1990-01-01)
The toxin was treated with [14C]trimethyloxonium tetrafluoroborate or [3H]glycine methyl ester in the presence of 1-ethyl-3(3-dimethylaminopropyl) carbodiimide. Esterification of separate carboxyl groups with [14C]trimethyloxonium tetrafluoroborate decreased the toxicity no more than two-fold. Blocking of any single carboxyl group with [3H]glycine

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/418/501/product-dating-information-06-25-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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