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900685

Sigma-Aldrich

2,4,6-Tri(p-tolyl)pyrylium tetrafluoroborate salt

≥95%

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About This Item

Empirical Formula (Hill Notation):
C26H23BF4O
CAS Number:
2713-21-5
Molecular Weight:
438.26
UNSPSC Code:
12161600
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

mp

298-303 °C

Application

Excitable by blue LEDs, this photocatalyst was reported by the Nicewicz laboratory for catalysis of O-aryl carbamothioates to S-aryl carbamothioates at ambient temperatures, an improvement from the elevated reaction temperatures traditionally needed in the Newman-Kwart rearrangment or palladium catalysis. Effective for scale-up or flow chemistry, this triarylpyrylium salt provides convenient access to thiophenols from phenols.
It can also catalyze visible light-initiated, living cationic polymerization of 4-methoxystyrene with methanol under metal-free conditions.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis
Cycloaddition Reactions Initiated by Photochemically Excited Pyrylium Salts

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Visible light photoinitiated metal-free living cationic polymerization of 4-methoxystyrene.
Perkowski A J, et al.
Journal of the American Chemical Society, 137(24), 7580-7583 (2015)

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Nicewicz Group – Professor Product Portal

The Nicewicz lab is focused on the discovery of new and powerful reaction methodologies that proceed via the intermediacy of highly reactive cation radical species. Included in these transformations are anti-Markovnikov selective additions of amines, alcohols, carboxylic acids, amides and mineral acids to alkenes.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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