ChemicalBook > CAS DataBase List > Trimethyloxonium Tetrafluoroborate

Trimethyloxonium Tetrafluoroborate

Product Name
Trimethyloxonium Tetrafluoroborate
CAS No.
420-37-1
Chemical Name
Trimethyloxonium Tetrafluoroborate
Synonyms
TriMethyloxoniuM Fluoroborate;triMethyloxoiuM tetrafluoroborate;trimethyl-oxoniu tetrafluoroborate;SKL1456;SKL1563;Me3OBF4;NSC 528455;oxonium tetrafL;trimethyloxidanium;Oxonium, trimethyl-
CBNumber
CB3184284
Molecular Formula
C3H9BF4O
Formula Weight
147.91
MOL File
420-37-1.mol
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Trimethyloxonium Tetrafluoroborate Property

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)
EPA Substance Registry System
Oxonium, trimethyl-, tetrafluoroborate(1-) (420-37-1)
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Safety

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 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29420000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
281077
Product name
Trimethyloxonium tetrafluoroborate
Purity
95%
Packaging
1g
Price
$40.8
Updated
2025/07/31
Sigma-Aldrich
Product number
281077
Product name
Trimethyloxonium tetrafluoroborate
Purity
95%
Packaging
10g
Price
$85.2
Updated
2025/07/31
TCI Chemical
Product number
T1507
Product name
Trimethyloxonium Tetrafluoroborate
Purity
>95.0%(T)
Packaging
5g
Price
$37
Updated
2025/07/31
TCI Chemical
Product number
T1507
Product name
Trimethyloxonium Tetrafluoroborate
Purity
>95.0%(T)
Packaging
25g
Price
$98
Updated
2025/07/31
Strem Chemicals
Product number
08-2500
Product name
Trimethyloxonium tetrafluoroborate, min. 95%
Packaging
5g
Price
$76
Updated
2024/03/01
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Trimethyloxonium Tetrafluoroborate Chemical Properties,Usage,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 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.

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.

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

115-10-6

109-63-7

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.

Trimethyloxonium Tetrafluoroborate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Trimethyloxonium Tetrafluoroborate manufacturers

Chongqing Chemdad Co., Ltd
Product
TRIMETHYLOXONIUM TETRAFLUOROBORATE 420-37-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99
Supply Ability
20tons
Release date
2025-04-24
Shaanxi Dideu New Materials Co. Ltd
Product
Trimethyloxonium Tetrafluoroborate 420-37-1
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000KGS
Release date
2025-04-12
Zibo Hangyu Biotechnology Development Co., Ltd
Product
Trimethyloxonium Tetrafluoroborate 420-37-1
Price
US $0.00-0.00/KG
Min. Order
100KG
Purity
99.9%
Supply Ability
20TONS
Release date
2023-10-10

420-37-1, Trimethyloxonium TetrafluoroborateRelated Search:


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  • CH33OBF4
  • C3H9BF4O
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  • B (Classes of Boron Compounds)
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  • Tetrafluoroborates
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