| Identification | More | [Name]
TRIMETHYLOXONIUM TETRAFLUOROBORATE | [CAS]
420-37-1 | [Synonyms]
TRIMETHYLOXONIUM TETRAFLUOROBORATE
trimethyl-oxoniutetrafluoroborate(1-)
trimethyloxonium tetrafluoroborate(1-)
Trimethyloxonium tetrafluoroborate 98+%
Trimethyloxoniumtetrafluoroborate,C24%min
Trimethyloxoniumtetrafluoroborate,min.95%
Oxonium, trimethyl-, tetrafluoroborate(1-)
Trimethyloxonium tetrafluoroborate 98%
trimethyl-oxoniu tetrafluoroborate
Trimethyloxonium tetrafluoroborate, 97+%
Trimethyloxonium tetrafluoroborate, min. 95% | [EINECS(EC#)]
206-994-4 | [Molecular Formula]
C3H9BF4O | [MDL Number]
MFCD00011798 | [Molecular Weight]
147.91 | [MOL File]
420-37-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystals | [Melting point ]
200 °C
| [storage temp. ]
2-8°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) | [Storage Precautions]
Store under inert gas;Moisture sensitive | [EPA Substance Registry System]
Oxonium, trimethyl-, tetrafluoroborate(1-) (420-37-1) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R14:Reacts violently with water.
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
3-10-21 | [Hazard Note ]
Corrosive/Freeze | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29420000 |
| Hazard Information | Back Directory | [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]
white to off-white crystals | [Uses]
Trimethyloxonium Tetrafluoroborate is a trialkylated oxonium used as a methylation agent in organic synthesis. | [Health Hazard]
Trimethyloxonium Tetrafluoroborate(420-37-1) 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]
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.
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