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341-02-6 - Triphenylcarbenium tetrafluoroborate, 98% - Trityl tetrafluoroborate - Trityl fluoroborate - A12949 - Alfa Aesar

A12949 Triphenylcarbenium tetrafluoroborate, 98%

CAS Number
341-02-6
Synonyms
Trityl tetrafluoroborate
Trityl fluoroborate

Size Price ($) Quantity Availability
10g 46.14
50g 187.46
250g 570.40
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Triphenylcarbenium tetrafluoroborate, 98%

MDL
MFCD00013120
EINECS
206-433-3

Chemical Properties

Formula
C19H15BF4
Formula Weight
330.13
Melting point
ca 207° dec.
Sensitivity
Moisture Sensitive
Solubility
Insoluble in water. Soluble in methanol.

Applications

It is applied in the abstraction of the ?-H atom of alcohols and their O-substituted derivatives results in oxidation to the ketones and in the oxidation of TMS ethers to ketones, secondary alcohols to ketones, and secondary diols to ?-hydroxy ketones. It is applied as a reactant involved in the synthesis of substituted dihydroazulene photo switches, carbene-based Lewis pairs for hydrogen activation, 1,3-Dipolar cycloaddition reactions for preparation of α-amino-β-hydroxy esters, oxidation of allenic compounds, Mukaiyama aldol addition reactions and ionic hydrogenation as a counteranion and ligand source.

Notes

Moisture sensitive. Store away from bases, water/moisture, heat and oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Store under inert gas. Keep it refrigerated.

Literature References

Louise Skov, et al. New synthetic route to substituted dihydroazulene photoswitches.Org Biomol Chem.,2011,9(19), 6498-6501.

J. Danielsson, et al. 1,3-Dipolar Cycloaddition of Azomethine Ylides to Aldehydes: Synthesis of anti a-Amino-ß-Hydroxy Esters.European J. Org. Chem.,2011,3607-613.

T. Yamaguchi, et al. Demethylation of an Allene Bearing Two Dimethoxythioxanthene Groups by Oxidation via a Vinyl Cation Intermediate.Aust. J. Chem.,2010,631638-1644.

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 ɑß-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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P280-P303+P361+P353-P305+P351+P338-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
5085649
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2942.00
TSCA
Yes

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