130318-01-3

Basic information

• Product Name: 2,3,4-TRIPHENYLPYRIDINE
• Synonyms: 2,3,4-TRIPHENYLPYRIDINE
• CAS NO: 130318-01-3
• Molecular Formula: C₂₃H₁₇N
• Molecular Weight: 307.39
• Mol File: 130318-01-3.mol

Chemical Properties

• Boiling Point: 398.982 °C at 760 mmHg
• Flash Point: 169.101 °C
• Appearance: /
• Density: 1.104g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 2,3,4-TRIPHENYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRIPHENYLPYRIDINE(130318-01-3)
• EPA Substance Registry System: 2,3,4-TRIPHENYLPYRIDINE(130318-01-3)

Safety Data

• Hazardous Substances Data: 130318-01-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3,4-Triphenylpyridine serves as a building block in organic synthesis, facilitating the creation of more complex molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Development:
2,3,4-TRIPHENYLPYRIDINE has been utilized in the development of pharmaceuticals due to its potential biological activities. Its structure can be modified to create new drug candidates, contributing to the advancement of medicinal chemistry.
Used in Organic Light-Emitting Diodes (OLEDs):
2,3,4-Triphenylpyridine has been incorporated into the design of OLEDs for electronic devices. Its light-emitting properties make it a suitable component for these devices, enhancing their performance and efficiency.
Used in Materials Science:
2,3,4-TRIPHENYLPYRIDINE has been studied for its potential applications in materials science, particularly as a light-emitting material for organic LEDs. Its properties contribute to the development of innovative materials with improved performance characteristics.

InChI:InChI=1/C23H17N/c1-4-10-18(11-5-1)21-16-17-24-23(20-14-8-3-9-15-20)22(21)19-12-6-2-7-13-19/h1-17H

Upstream product

• 130317-97-4 N-(1,2-diphenylethenyl)-P,P-diphenylphosphinic amide 
• 104-55-2 3-phenyl-propenal 
• 501-65-5 diphenyl acetylene 
• 253284-70-7 (Z)-3-iodo-3-phenylacrylaldehyde 
• 952-06-7 deoxybenzoin oxime 
• 128080-52-4 (E)-1,2-diphenylethan-1-one O-acetyl oxime 
• 14804-59-2 3-bromo-3-phenylacrylaldehyde 
• 19690-01-8 1,2-diphenylethanone O-acetyl oxime 

Relevant articles and documents

Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

Pyridine formation with oxime acetates as the building blocks under metal-free conditions is described. Ammonium iodide has proved to be a highly efficient promoter for oxime N-O bond reduction and subsequent condensation reactions, whereby it played a dual-function role in the transformation. While the three-component reaction of oxime acetates, benzaldehydes, and 1,3-dicarbonyls proceeded well with the assistance of a stoichiometric amount of ammonium iodide, the condensation of oximes and acroleins was enabled by using a catalytic initiator to afford substituted pyridines. By this protocol, substituted pyridine products were generated in moderate to excellent yields with tolerance towards a broad range of functional groups.

Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

Transition-metal-catalyzed synthesis of N-heterocycles from oximes has been previously well established. In this paper, for the first time a metal-free protocol with the combinational employment of iodine and triethylamine has been demonstrated to be effective to trigger the oxime-based synthesis of pyridines with high chemo-selectivity and wide functional group tolerance. A broad range of functional pyridines were prepared in moderate to excellent yields. While neither iodine nor triethylamine could trigger this transformation, mechanistic experiments indicated a radical pathway for the reaction. The resultant 2-aryl-substituted pyridines have been proved to be versatile building blocks in a range of transition-metal-catalyzed C-H functionalization reactions. (Chemical Equation Presented).

Modular pyridine synthesis from oximes and enals through synergistic copper/iminium catalysis

We describe here a [3+3]-type condensation reaction of O-acetyl ketoximes and α,β-unsaturated aldehydes that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine). This redox-neutral reaction allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst, which would initially reduce the oxime N-O bond to generate a nucleophilic copper(II) enamide and later oxidize a dihydropyridine intermediate to the pyridine product.

Palladium-catalyzed multi-component synthesis of steroidal A- and D-ring fused 5,6-disubstituted pyridines under microwave irradiation

The preparation of steroidal A-, D-ring fused 5,6-disubstituted pyridines and nonsteroidal substituted pyridines is described form Pd(OAc)2 catalyzed multi-component reaction of steroidal/nonsteroidal β-halovinyl aldehyde, alkyne and benzylamin

Highly efficient synthesis of isoquinolines via nickel-catalyzed annulation of 2-iodobenzaldimines with alkynes: Evidence for dual pathways of alkyne insertion

(Chemical Equation Presented) A wide range of substituted isoquinolines were synthesized via a highly efficient nickel-catalyzed annulation of the tert-butyl imines of 2-iodobenzaldehydes and various alkynes; examination of the regiochemistry of isoquinol

Synthesis of isoquinolines and pyridines by the palladium-catalyzed iminoannulation of internal alkynes

A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)2, an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.

A Novel Formation of Phenyl-Substituted Pyridines by the Reaction of N-(Diphenylphosphinyl)-1-azaallyl Anions with α,β-Unsaturated Carbonyl Compounds. A New Synthetic Equivalent of Primary Vinylamines

The N-phosphinyl-1-azaallyl anions, which were derived from the corresponding imine or enamine reacted with α,β-unsaturated carbonyl compounds to afford phenyl-substituted pyridines along with 1-propanone and 1,5-pentanedione derivatives.A plausible mechanism involving a sequence of Michael addition and intramolecular aza-Horner-Wittig reaction is described, and the 1-azaallyl anions were found to behave as a synthetic equivalent of primary vinylamines.