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Trimethyloxonium Tetrafluoroborate

CAS No.
420-37-1
Chemical Name:
Trimethyloxonium Tetrafluoroborate
Synonyms
Me3OBF4;TriMethyloxoniuM Fluoroborate;trimethyloxonium tetrafluoroborate(1-);trimethyloxidanium;triMethyloxoiuM tetrafluoroborate;rimethyloxonium Tetrafluoroborate;trimethyl-oxoniu tetrafluoroborate;SKL1456;SKL1563;NSC 528455
CBNumber:
CB3184284
Molecular Formula:
C3H9BF4O
Molecular Weight:
147.91
MDL Number:
MFCD00011798
MOL File:
420-37-1.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 01:02:58
Product description Number Pack Size Price
Trimethyloxonium tetrafluoroborate 95% 281077 1g $43.4
Trimethyloxonium tetrafluoroborate 95% 281077 10g $90.8
Trimethyloxonium Tetrafluoroborate >95.0%(T) T1507 5g $37
Trimethyloxonium Tetrafluoroborate >95.0%(T) T1507 25g $98
Trimethyloxonium tetrafluoroborate, min. 95% min.95% 08-2500 5g $80
More product size

Trimethyloxonium Tetrafluoroborate Properties

Melting point 200 °C
storage temp. Store at +2°C to +8°C.
solubility Soluble in nitrobenzene, nitromethane, chloroform, hot acetone, liquid sulfur dioxide. Slightly soluble in dichloromethane. Insoluble in common organic solvents.
form Crystals
color White to off-white
Sensitive Moisture Sensitive
BRN 3597303
InChI InChI=1S/C3H9O.BF4/c1-4(2)3;2-1(3,4)5/h1-3H3;/q+1;-1
InChIKey JDFKFXJJAIJXPP-UHFFFAOYSA-M
SMILES [B-](F)(F)(F)F.[O+](C)(C)C
CAS DataBase Reference 420-37-1(CAS DataBase Reference)
FDA UNII BFC3NMU8S8
EPA Substance Registry System Oxonium, trimethyl-, tetrafluoroborate(1-) (420-37-1)
UNSPSC Code 12352107
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Corrosion (GHS05)
GHS05
Signal word  Danger
Hazard statements  H314
Precautionary statements  P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
PPE Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes  C
Risk Statements  14-34
Safety Statements  26-36/37/39-43-45
RIDADR  UN 3261 8/PG 2
WGK Germany  3
3-10-21
Hazard Note  Corrosive/Freeze
TSCA  TSCA listed
HazardClass  8
PackingGroup  II
HS Code  29420000
Storage Class 8A - Combustible corrosive hazardous materials
Hazard Classifications Skin Corr. 1B
Limited Quantities 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
NFPA 704
1
3 2
W

Trimethyloxonium Tetrafluoroborate price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 281077 Trimethyloxonium tetrafluoroborate 95% 420-37-1 1g $43.4 2026-04-30 Buy
Sigma-Aldrich 281077 Trimethyloxonium tetrafluoroborate 95% 420-37-1 10g $90.8 2026-04-30 Buy
TCI Chemical T1507 Trimethyloxonium Tetrafluoroborate >95.0%(T) 420-37-1 5g $37 2026-04-30 Buy
TCI Chemical T1507 Trimethyloxonium Tetrafluoroborate >95.0%(T) 420-37-1 25g $98 2026-04-30 Buy
Strem Chemicals 08-2500 Trimethyloxonium tetrafluoroborate, min. 95% min.95% 420-37-1 5g $80 2026-04-30 Buy
Product number Packaging Price Buy
281077 1g $43.4 Buy
281077 10g $90.8 Buy
T1507 5g $37 Buy
T1507 25g $98 Buy
08-2500 5g $80 Buy

Trimethyloxonium Tetrafluoroborate Chemical Properties,Uses,Production

Description

Trimethyloxonium tetrafluoroborate (TMO), a trialkyloxonium salt, is a white salt at ambient temperature that can be added directly to reaction media to carry out the methylation of reactive, acidic analytes. The main drawback associated with the employment of TMO is the generation of tetrafluoroboric acid (HBF4), which may interfere with the analysis of acid-sensitive analytes and cause column degradation over time. However, the effects of this acid can be countered by neutralization with inorganic bases like sodium or potassium bicarbonate during the sample preparation step before instrument injection. This approach has proven crucially useful in analysing phosphonic and sulfonic acids related to organophosphorus-based nerve agents. TMO could be employed as a derivatizing agent in the methylation of a panel of environmentally relevant chlorinated phenols. It is also used in neutral and basic solutions for the selective methylation of the carboxyl groups of protohemin IX, hematohemin, and heme a[1-2].

Chemical Properties

This substance is a white to off-white crystals that is prone to water sensitivity and displays a level of hygroscopicity.

Uses

Trimethyloxonium tetrafluoroborate act as a avmethylating agent and activates C-X multiple bonds. It is involved in the esterification of polyfunctional carboxylic acids. It acts as a catalyst in the polymerization of cyclic sulfides and ethers. Further, it is used in Beckmann rearrangement of oximes.

Uses

Trimethyloxonium Tetrafluoroborate is a trialkylated oxonium used as a methylation agent in organic synthesis. It is a reagent for the methylation of hydroxyl groups recently used in a complex, multistep synthesis directed towards spirastrellolide, a marine natural product.

Health Hazard

Trimethyloxonium Tetrafluoroborate is a potent alkylating agent, with its non-volatile nature reducing associated hazards. Nevertheless, it produces strong acids upon contact with water, so it is important to exercise caution and prevent water contact during its application.

Synthesis

Dimethyl ether

115-10-6

Boron trifluoride diethyl etherate

109-63-7

Trimethyloxonium Tetrafluoroborate

420-37-1

The general procedure for the preparation of trimethoxonium tetrafluoroborate is as follows (adapted with minor modifications from TJ. Curphey, Org. Synth., Coll. vol. 6, p. 1019 (1988)): 1. add 80 mL of dichloromethane (DCM) to a 500 mL three-necked round-bottomed flask (equipped with an N2 inlet, 60 mL pressure-equalizing dropping funnel, magnetic stirring bar, and rubber septum, and marked at approximately 190 mL) that has been pre-dried in an oven, under the protection of dry nitrogen gas. 2. 33.3 mL (270 mmol) of boron trifluoride ether compound was added, followed by cooling the mixture in a dry ice-acetone bath. 3. condense the DME into the DCM solution through a needle inserted through the rubber septum, which should remain just below the liquid level until the total volume of liquid reaches the 190mL mark. 4. add 24.1mL (307mmol) of epichlorohydrin dropwise over approximately 15 minutes with vigorous stirring (note: the mixture will become very viscous and may need to be rotated manually to ensure adequate stirring). 5. Remove the cooling bath and continue to vigorously stir the mixture overnight at room temperature. 6. Upon completion of the reaction, the resulting solid product was collected by filtration through a medium glass-filled Brinell's funnel, which had been pre oven-dried, under a stream of N2 gas. 7. The flask and filter were rinsed with dichloromethane (2 x 100mL) to remove the solids. 8. After drying under nitrogen protection, 29.4 g (98% yield) of free flowing white solid trimethoxonium tetrafluoroborate was obtained. 9. Store the product in a pre-oven dried glass vial in a nitrogen protected refrigerator.

References

[1] Carlos A Valdez, Roald N Leif, Edmund P Salazar. “Trimethyloxonium-mediated methylation strategies for the rapid and simultaneous analysis of chlorinated phenols in various soils by electron impact gas chromatography-mass spectrometry.” Scientific Reports (2022): 1401.
[2] R T Dean, D E Hultquist, L J DeFilippi. “Esterification of hemins with trimethyloxonium tetrafluoroborate.” Analytical biochemistry 76 l (1976): 1–8.

115-10-6
109-63-7
420-37-1
Synthesis of Trimethyloxonium Tetrafluoroborate from Dimethyl ether and Boron trifluoride diethyl etherate
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