420-37-1

Basic information

• Product Name: TRIMETHYLOXONIUM TETRAFLUOROBORATE
• 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%
• CAS NO: 420-37-1
• Molecular Formula: BF₄*C₃H₉O
• Molecular Weight: 147.91
• EINECS: 206-994-4
• Product Categories: B (Classes of Boron Compounds);Iodonium Sulfonium & Oxonium Compounds;Oxonium Compounds;Tetrafluoroborates;Alkyl Transfer;C-X Bond Formation (Non-Halogen);Synthetic Reagents;halometallate salts
• Mol File: 420-37-1.mol

Chemical Properties

• Melting Point: 200 °C
• Appearance: White to off-white/Crystals
• Storage Temp.: 2-8°C
• Solubility: Soluble in nitrobenzene, nitromethane, chloroform, hot acetone,
• Sensitive: Moisture Sensitive
• BRN: 3597303
• CAS DataBase Reference: TRIMETHYLOXONIUM TETRAFLUOROBORATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLOXONIUM TETRAFLUOROBORATE(420-37-1)
• EPA Substance Registry System: TRIMETHYLOXONIUM TETRAFLUOROBORATE(420-37-1)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-43-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 3-10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 420-37-1(Hazardous Substances Data)

Usage

Uses

1. Organic Synthesis:
Trimethyloxonium tetrafluoroborate is used as a methylation agent in organic synthesis, facilitating the transfer of a methyl group to other molecules, which is crucial for the formation of various organic compounds.
2. Activation of C-X Multiple Bonds:
In the field of organic chemistry, this compound acts as an activating agent for C-X multiple bonds, enhancing the reactivity of these bonds and enabling further chemical reactions.
3. Esterification of Polyfunctional Carboxylic Acids:
Trimethyloxonium tetrafluoroborate is employed in the esterification process of polyfunctional carboxylic acids, which is an essential step in the synthesis of various organic compounds and materials.
4. Polymerization Catalyst:
Trimethyloxonium tetrafluoroborate serves as a catalyst in the polymerization of cyclic sulfides and ethers, which are important processes in the production of polymers with specific properties and applications.
5. Beckmann Rearrangement:
Trimethyloxonium tetrafluoroborate is used in the Beckmann rearrangement of oximes, a significant chemical reaction that transforms oximes into amides, which are vital building blocks in the synthesis of various pharmaceuticals and organic compounds.
6. Reagent for Hydroxyl Group Methylation:
Recently, it has been used as a reagent for the methylation of hydroxyl groups in complex, multistep syntheses, such as the synthesis of spirastrellolide, a marine natural product with potential biological activities.

InChI:InChI=1/C3H9O.B.4FH/c1-4(2)3;;;;;/h1-3H3;;4*1H/q+1;+3;;;;/p-4

Upstream product

• 186581-53-3 diazomethane 
• 115-10-6 Dimethyl ether 
• 623-73-4 diazoacetic acid ethyl ester 
• 368-39-8 triethyloxonium fluoroborate 
• 74-88-4 methyl iodide 
• 33613-52-4 dimethylphenyl sulfonium tetrafluoroborate 
• 593-53-3 Methyl fluoride 
• 460-13-9 propyl fluoride 
• 75-09-2 dichloromethane 
• 109-63-7 boron trifluoride diethyl etherate 
• 18346-68-4 dimethoxymethylium tetrafluoroborate 

Downstream Products

• 153068-59-8 3-methyl-[1,3]thiazinan-2-ylideneamine 
• 70375-66-5 5-imino-2,3-dimethyl-2,5-dihydro-isothiazole-4-carboxylic acid ethyl ester 
• 57440-15-0 N-methyl-N-(2-hydroxyethyl)benzamide 
• 34551-29-6 4-methyl-5-phenylimino-Δ²-1,2,3,4-thiatriazoline 
• 34684-49-6 3,4-dimethyl-2-phenethyl-thiazolidine 
• 5799-67-7 dimethyl(methylthio)sulfonium tetrafluoroborate 

Relevant articles and documents

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Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

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Microbicides

Compounds of formula I STR1 and possible isomers and isomeric mixtures thereof, wherein a) X is CH2 F or CHF2 ; Y is CH and Z is OMe, or b) X is CH2 F or CHF2 ; Y is a nitrogen atom and Z is OMe or NHCH3, and wherein also m is 0, 1, 2, 3, 4 or 5 and U represents identical or different substituents selected from halogen, cyano, nitro, C1 -C12 alkyl, C3 -C8 cycloalkyl, C3 -C6 alkenyl, C3 -C6 alkenyloxyiminomethyl, C1 -C4 alkoxy, C1 -C4 alkoxyiminomethyl, C1 -C2 haloalkyl, C1 -C2 haloalkoxy, unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy and unsubstituted or substituted benzyl or represents substituents at two adjacent positions of the phenyl ring of formula I that define a fused hydrocarbon bridge so as to form a larger hydrocarbon ring having up to 14 carbon atoms, are suitable for controlling and preventing microorganisms, insects and Acarina on plants. They can be used in the form of commercially customary formulated compositions.

Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine

Practical methodology for the bis-O-methylation of (3S)-isopropyl-piperazine-2,5-dione 4 on a 45 g scale to generate Schollkopf's bis-lactim ether chiral auxiliary (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine 1 has been developed. Monomethylated intermediates 5 and 6 are reported for the first time. The gelling effects of 4 in a range of common solvents are also described.

Correlations of pKlgMe with Reduction Potentials

The quantitative indices for the ability of leaving groups to depart from C atoms are pKlgMe. In the cases of methyl transfers from arenesulfonates, these parameters have correlated a large number of nucleophilic data. A new scale of these parameters has been defined from methyl transfer data between phenylmethyl thioethers. The pKlgMe data from both sets of compounds correlated with both experimental E1/2 values and ELUMO values from computational chemistry. These correlations support the SCM model of Shaik et al. which requires the leaving group to display some SET character in an SN2 transition state.

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Onium Ylide Chemistry. 2. Methylenedialkyloxonium Ylides

We report evidence for the long sought after methylenedialkyloxonium ylides from methyloxonium ions by two independent routes, proving their intermediate formation through derived product analysis.Reaction of trimethyloxonium salts with sodium hydride results in competing proton abstraction besides methane formation (hydride methylation).Subsequent methylation of the formed methylenedimethyloxonium ylide by excess trimethyloxonum ion is resulting in C1 --> C2 conversion and formation of dimethylethyloxonium ion which with sodium hydride gives ethane (and methane) or by β-elimination ethylene.Besides expected fluoride alkylation products, i.e., alkyl fluorides and fluorosilanes, fluoride-induced desylilation of dimethyl((trimethylsilyl)methyl)oxonium tetrafluoroborate also results in the formation of methylenedimethyloxonium ylide giving via subsequent methylation and cleavage methyl ethyl ether and ethyl fluoride.