Trimethyloxonium tetrafluoroborate

Base Information

• Chemical Name: Trimethyloxonium tetrafluoroborate
• CAS No.: 420-37-1
• Molecular Formula: C3H9BF4O
• Molecular Weight: 147.908
• Hs Code.: 29420000
• European Community (EC) Number: 206-994-4
• DSSTox Substance ID: DTXSID20883377
• Wikipedia: Trimethyloxonium_tetrafluoroborate
• Wikidata: Q204202
• Mol file: 420-37-1.mol

Synonyms:TMOTFB;trimethyloxonium tetrafluoroborate(1-)

Chemical Property of Trimethyloxonium tetrafluoroborate

Chemical Property:

• Appearance/Colour: white to off-white crystals
• Melting Point: 200 °C
• PSA: 9.23000
• LogP: 1.72810
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in nitrobenzene, nitromethane, chloroform, hot acetone,
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 148.0682577
• Heavy Atom Count: 9
• Complexity: 27.1

Purity/Quality:

99% ^*data from raw suppliers

Trimethyloxonium tetrafluoroborate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-43-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [B-](F)(F)(F)F.C[O+](C)C
• Uses: Trimethyloxonium Tetrafluoroborate is a trialkylated oxonium used as a methylation agent in organic synthesis. 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. Reagent for the methylation of hydroxyl groups recently used in a complex, multistep synthesis directed towards spirastrellolide, a marine natural product.

Technology Process of Trimethyloxonium tetrafluoroborate

There total 15 articles about Trimethyloxonium tetrafluoroborate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Dimethyl ether (115-10-6,157621-61-9) + boron trifluoride diethyl etherate (109-63-7) → trimethoxonium tetrafluoroborate (420-37-1)

Guidance literature:

With epichlorohydrin; In dichloromethane; Cooling with acetone-dry ice; Inert atmosphere;

Reference yield: 92.0%

Dimethyl ether (115-10-6,157621-61-9) → trimethoxonium tetrafluoroborate (420-37-1)

Guidance literature:

With boron trifluoride diethyl etherate; epichlorohydrin; In dichloromethane; at -20 ℃;

DOI:10.1016/S0957-4166(97)00623-X

Reference yield: 17.0%

→ trimethoxonium tetrafluoroborate (420-37-1)

Guidance literature:

upstream raw materials:

diazomethane

Dimethyl ether

diazoacetic acid ethyl ester

triethyloxonium fluoroborate

Downstream raw materials:

3-methyl-[1,3]thiazinan-2-ylideneamine

5-imino-2,3-dimethyl-2,5-dihydro-isothiazole-4-carboxylic acid ethyl ester

N-tert-butyl-acetimidic acid methyl ester

dimethyl(methylthio)sulfonium tetrafluoroborate

Refernces

• 1、 Kilpin, Kelly J.,Paul, Ursula S. D.,Lee, Ai-Lan,Crowley, James D.. "Gold(i) "click" 1,2,3-triazolylidenes: Synthesis, self-assembly and catalysis". supporting information; experimental part. p. 328 - 330. Retrieved 2011/03/17.
• 2、 -. "Chemical synthesis of S-adenosyl-L-methionine with enrichment of ( S,S)-isomer". . . Retrieved 2008/06/13.