801-06-9

Basic information

• Product Name: 2,4,6-Triphenyl-4H-pyran
• Synonyms: 2,4,6-Triphenyl-4H-pyran
• CAS NO: 801-06-9
• Molecular Formula: C₂₃H₁₈O
• Molecular Weight: 310.39
• Mol File: 801-06-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4,6-Triphenyl-4H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Triphenyl-4H-pyran(801-06-9)
• EPA Substance Registry System: 2,4,6-Triphenyl-4H-pyran(801-06-9)

Safety Data

• Hazardous Substances Data: 801-06-9(Hazardous Substances Data)

Usage

General Description

2,4,6-Triphenyl-4H-pyran is a chemical compound with a molecular formula C24H20O. It is a derivative of the heterocyclic compound pyran and is characterized by a unique chemical structure containing three phenyl groups. 2,4,6-Triphenyl-4H-pyran is commonly used in organic synthesis reactions and is known for its fluorescent properties, making it useful in the development of fluorescent probes and dyes. It also exhibits potential medicinal properties and has been studied for its potential applications in the field of pharmaceuticals, particularly in the development of new drugs. Overall, 2,4,6-Triphenyl-4H-pyran is a versatile compound with various potential applications in the fields of chemistry, materials science, and medicine.

Upstream product

• 6263-84-9 1,3,5-triphenyl-1,5-pentanedione 
• 1484-88-4 2,4,6-triphenylpyrilium perchlorate 
• 448-61-3 2,4,6-triphenylpyrylium tetrafluoroborate 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 76162-49-7 1,3,5-Triphenyl-2-pentene-1,5-dione 
• 125179-34-2 2,4,6-triphenyl-3-formyl-4H-pyran 
• 57314-28-0 (3,5-Diphenyl-furan-2-yl)-phenyl-methanone 
• 85017-65-8 2,4,6-triphenyl-4H-selenopyran 

Relevant articles and documents

Facile and Stereospecific Synthesis of Various Dienones Using Task-specific Ionic Liquid/Borohydride as Stable and Promoted Hydrogen Release Reagent

In this work, for the first time, task-specific ionic liquid, 1-n-butyl-3-methylimidazolium borohydride ([bmim]BH4), was used as the medium as well as reagent for the regiospecific reduction of triarylpyrylium perchlorates to provide aromatic d

Substituent effects in cyanoborohydride reductions of heterocyclic aromatic cations

First and second wave E1/2redn potentials have been measured by cyclic voltammetry for a set of fifteen 2,6-diphenyl-4-(X-phenyl)-pyrylium, -thiopyrylium and -N-methylpyridinium tetrafluoroborates, with X = p-CH3, -H, m-Cl, p-CF3 and m,m-(CF3)2.There are linear correlations between Hammett substituent constants and scaled potentials (E/0.05915) giving slopes of ρ = 2.59+/-0.06 (r2 = 0.9984), 2.38+/-0.07 (r2 = 0.9973) and 3.10+/-0.16 (r2 = 0.9918), respectively, for the first wave potentials.Products, rates and kinetic hydrogen isotope effects for reductions of the cations with sodium and tetrabutylammonium cyanoborohydride in acetonitrile solution have been determined.Reaction of the thiopyrylium 2 (X = H) yields kinetically controlled 54:46 mixture of the 4H- and 2H-thiopyrans.With the pyrylium ion 1 (X = H) the 4H- to 2H-ratio is 24:76 with the 2H-pyran suffering electrocyclic ring opening to 1,3,5-triphenylpentadienal.Product ratios are weakly sensitive to substituents on the 4-phenyl, with electron withdrawing groups increasing the amount of 2H-product for both thiopyryliums and pyrylium cations.Reductions are first order in cation and cyanoborohydride.For sodium cyanoborohydride and 2,4,6-triphenylpyrylium, k(25 deg C) = 65.6 dm3 mol-1 s-1 and for 2,4,6-triphenylthiopyrylium. k(25 deg C) = 16.7 dm3 mol-1 s-1, with kinetic isotope effects kBH3CN/kBD3CN) of 1.17 and 1.68, respectively.Logarithms of rate constants correlate with Hammett constants giving ρ = 1.46+/-0.06 (r2 = 0.9951) for the pyrylium series and ρ = 1.12+/-0.08 (r2 = 0.9831) for the thiopyryliums.The N-methylpyridinium ions do not react with cyanoborohydride.The X-ray crystal structure of 2,4,6-triphenyl-N-methylpyridinium tetrafluoroborate has been determined.Dihedral angles about bonds from the pyridinium ring to the 2- and 6-phenyls are larger than corresponding angles in 2,4,6-triphenylpyrylium and 2,4,6-triphenylthiopyryliums and are ascribed to relief of non-bonded interactions between the 2- and 6-phenyls and the N-methyl group.

Δ3-DIHYDROPYRANS AND TETRAHYDROPYRANS BY REDUCTION OF PYRYLIUM SALTS WITH SODIUM BOROHYDRIDE IN ACETIC ACID

The major reduction products with triacetoxyborohydride (NaBH4 in AcOH) of 2,4,6-trisubstituted pyrylium salts bearing alkyl substituents in the 2- and/or 6-position are the Δ3-dihydropyrans with cis 2- and 6-substituents and all-cis-2,4,6-trisubstituted tetrahydropyrans. Δ3-dihydropyrans are shown to be formed via 2H-pyrans by a 1,4 reduction while tetrahydropyrans result from 4H-pyrans by reduction of both enol-ether double bonds.