23809-15-6

Basic information

• Product Name: 2,4,6-triphenylpyranyl
• Synonyms: 2,4,6-triphenylpyranyl
• CAS NO: 23809-15-6
• Molecular Weight: 309.387
• Mol File: 23809-15-6.mol

Chemical Properties

• CAS DataBase Reference: 2,4,6-triphenylpyranyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-triphenylpyranyl(23809-15-6)
• EPA Substance Registry System: 2,4,6-triphenylpyranyl(23809-15-6)

Safety Data

• Hazardous Substances Data: 23809-15-6(Hazardous Substances Data)

Upstream product

• 448-61-3 2,4,6-triphenylpyrylium tetrafluoroborate 
• 1484-88-4 2,4,6-triphenylpyrilium perchlorate 

Downstream Products

• 76162-49-7 1,3,5-Triphenyl-2-pentene-1,5-dione 
• 591-50-4 iodobenzene 
• 23800-57-9 1,3,5-triphenylpent-2-en-1,5-dione 
• 55118-49-5 2,4,6-triphenylpyrylium acetate 
• 4735-00-6 1,3,5-triphenylpent-2,4-dien-1-one 
• 57314-28-0 (3,5-Diphenyl-furan-2-yl)-phenyl-methanone 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 34557-54-5 methane 
• 124-38-9 carbon dioxide 
• 13179-84-5 2,4,6-triphenylpyrylium bromide 

Relevant articles and documents

Polarographic reduction of pyrylium salts

The polarographic reduction of several pyrylium perchlorates in buffered and unbuffered solution was investigated at DME. In 0.1m LiCl-DMF, two waves are observed. The first wave is reversible and diffusion controlled representing the uptake of one electron, whereas the second wave is a catalytic reduction of the perchlorate ion. In buffered solutions (pH ≤ 5), only one wave is obtained and its i decreases with pH due to the partial conversion of the pyrylium salt into a pseudo-base. The rate of conversion, electron affinities, ionization potentials and the energy levels of HOMO and LUMO of these compounds have been computed and a linear correlation shown to exist between the spectroscopic data and the redox potentials.

Free Radicals Produced from the Derivatives of Pyrylium Salts in Solution by Photoillumination

The photoreactions of 2,4,6-triphenyl- (TPP), 2-t-butyl-4,6-diphenylpyrylium (2BDPP) and 2,4,6-triphenylthiopyrylium (TPTP) salts in tetrahydrofuran (THF) and/or 1,2-dimethoxyethane were investigated.Photoproducts were identified to be pyranyl radicals on the basis of photochemical behavior and ESR spectra.Quantum yields of one-electron reduction of TPP, 2BDPP, and TPTP were obtained to be 0.21, 0.047, and 0.53, respectively.The hf coupling constants of protons in the radicals were determined by simulation.The photoillumination of TPP in THF at low temperatures revealed that a certain intermediate radical species was involved in this one-electron photoreduction.

The role of aromatic radical cations and benzylic cations in the 2,4,6-triphenylpyrylium tetrafluoroborate photosensitized oxidation of ring-methoxylated benzyl alcohols in CH2Cl2 solution

A steady-state and laser flash photolysis (LFP) study of the TPPBF 4-photosensitized oxidation of ring-methoxylated benzyl alcohols has been carried out. Direct evidence on the involvement of intermediate benzyl alcohol radical cations and benzylic cations in these reactions has been provided through LFP experiments. The reactions lead to the formation of products (benzaldehydes, dibenzyl ethers, and diphenylmethanes) whose amounts and distributions are influenced by the number and relative position of the methoxy substituents. This behavior has been rationalized in terms of the interplay between the stabilities of benzyl alcohol radical cations and benzyl cations involved in these processes. A general mechanism for the TPPBF 4-photosensitized reactions of ring-methoxylated benzyl alcohols has been proposed, where the a-OH group of the parent substrate acts as the deprotonating base promoting α-C-H deprotonation of the benzyl alcohol radical cation (formed after electron transfer from the benzyl alcohol to TPP*) to give a benzyl radical and a protonated benzyl alcohol, precursor of the benzylic cation. This hypothesis is in contrast with previous studies, where formation of the benzyl cation was suggested to occur from the neutral benzyl alcohol through the Lewis acid action of excited TPP+ (TPP*).