tetrafluoroboranuide; trimethyloxidanium

• ChemBase ID: 99822
• Molecular Formular: C3H9BF4O
• Molecular Mass: 147.9075728
• Monoisotopic Mass: 148.06825819
• SMILES: [B-](F)(F)(F)F.[O+](C)(C)C
• Canonical SMILES: F[B-](F)(F)F.C[O+](C)C
• InChI: InChI=1S/C3H9O.BF4/c1-4(2)3;2-1(3,4)5/h1-3H3;/q+1;-1
• InChIKey: CZVZBKHWOFJNCR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrafluoroboranuide; trimethyloxidanium
• IUPAC Traditional name: trimethyloxidanium tetrafluoroborate
• Synonyms: Trimethyloxonium tetrafluoroborate 95%; Trimethyloxonium tetrafluoroborate; Trimethyloxonium fluoborate; Trimethyloxonium tetrafluoroborate; 三甲基氧鎓四氟硼酸盐; 三甲基钖四氟硼酸

Database IDs

• CAS Number: 420-37-1
• EC Number: 206-994-4
• MDL Number: MFCD00011798
• Beilstein Number: 3597303
• PubChem SID: 24856967; 162086069; 24889679
• PubChem CID: 2735153
• Chemspider ID: 2016863
• Wikipedia Title: Trimethyloxonium_tetrafluoroborate

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -1.13
• LogD (pH = 7.4): -1.13
• Log P: -1.13
• Molar Refractivity: 6.0052 cm^3
• Polarizability: 3.1085358 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200°C; ca 190°C dec.
• Flash Point: >110°C

Safety Information

• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34; 34
• Safety Statements: 26-36/37/39-43-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (T); 95%; 96%
• Grade: purum
• Linear Formula: (CH3)3O(BF4)

DETAILS

Apollo Scientific Ltd - PC7865

Versatile mild methylating agent

Sigma Aldrich - 281077

Application
Reagent for the methylation of hydroxyl groups recently used in a complex, multistep synthesis directed towards spirastrellolide, a marine natural product.1
Packaging
1, 10 g in poly bottle

Sigma Aldrich - 92605

Application
A Meerwein salt, strong electrophilic methylating agent

REFERENCES

• Trialkyloxonium salts, also known as Meerwein's salts, are powerful alkylating agents under mild conditions. For general reactions of trialkyloxonium salts, see Triethyloxonium tetrafluoroborate, A14420. For a brief feature of their uses in synthesis, see: Synlett, 195 (2004).
• Alkylation of ethylene thioacetals proceeds only to the monoalkyl salt unless water is added, when the thioacetal is cleaved to give the carbonyl compound and the tetraalkyl ethane bis-sulfonium salt: Synthesis, 135 (1981). Alkylation on S to promote leaving group ability has also been used in a synthesis of oxiranes from ?-hydroxy sulfides: J. Am. Chem. Soc., 95, 3429 (1973); J. Chem. Soc., Chem. Commun., 714 (1975).
• N,N-Dialkyl arylcarboxamides, useful as substrates for directed metallation reactions, can be converted to methyl esters in high yield: Tetrahedron, 56, 9875 (2000).