Triphenylcarbenium tetrafluoroborate

• Catalog No.: A12949
• CAS Number: 341-02-6
• M. F.: C19H15BF4
• M. W.: 330.1270128
• Purity: 98%

SYNONYMS

• Title: 三苯基四氟硼酸碳
• IUPAC name: tetrafluoroboranuide; triphenylmethylium
• IUPAC Traditional name: triphenylmethylium tetrafluoroborate
• Synonyms: Trityl fluoroborate; Trityl tetrafluoroborate

DATABASE IDS

• EC Number: 206-433-3
• CAS Number: 341-02-6
• MDL Number: MFCD00013120
• Beilstein Number: 5085649

PROPERTIES

• Purity: 98%
• Melting Point: ca 207°C dec.
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• The trityl cation abstracts hydride ion from a variety of substrates:
• Cycloheptatriene gives the tropylium cation: J. Am. Chem. Soc., 79, 4557 (1957).
• With 1,3-Dithiane, A10505, gives the electrophilic dithienium salt which can react with silyl enol ethers to give ɑ-formyl or ɑ-methyl carbonyl compounds: Tetrahedron Lett., 22, 2829, 2833 (1981).
• Abstraction of the ɑ-H atom of alcohols and their O-substituted derivatives results in oxidation to the ketones:
• Oxidation of TMS ethers to ketones: J. Org. Chem., 41, 1479 (1976); secondary alcohols to ketones, and secondary diols to ɑ-hydroxy ketones: Tetrahedron Lett., 2771 (1978). Ketones can similarly be oxidized to ɑ?-unsaturated ketones by hydride abstraction from their silyl enol ethers: J. Org. Chem., 42, 3961 (1977); Synthesis, 736 (1979).
• The trityl cation is also useful for the oxidative cleavage of the 4-methoxybenzyl protecting group from secondary alcohols: J. Org. Chem., 49, 51 (1984).