52806-02-7

Usage

Chemical Family

1-methyl-2-phenylpyridinium iodide belongs to the family of pyridinium compounds.

Charge

It is a positively charged molecule due to the presence of the pyridinium group.

Research Use

Commonly used in research as a neurotoxin to study Parkinson's disease.

Neuronal Selectivity

It has been shown to selectively destroy dopaminergic neurons.

Biochemical and Pharmacological Studies

Used to understand the mechanisms of cell death and the neurotoxic effects of certain chemicals.

Organic Cation Transporter

It is a known substrate for the organic cation transporter.

Uptake and Accumulation

Its uptake and accumulation in cells have been extensively studied.

Solubility

1-methyl-2-phenylpyridinium iodide is a polar compound that is highly soluble in water and organic solvents, making it suitable for use in various experimental settings.

Upstream product

• 1008-89-5 2-phenylpyridine 
• 74-88-4 methyl iodide 
• 960-16-7 tributylphenylstannane 
• 52693-56-8 2-bromo-1-methyl-pyridinium iodide 
• 109-04-6 2-bromo-pyridine 
• 98-80-6 phenylboronic acid 

Downstream Products

• 75954-40-4 1-methyl-2-phenyl-1,2,3,6-tetrahydropyridine 
• 75954-42-6 (2Z,4E)-5-phenylpenta-2,4-dienyl-N,N-dimethylamine 
• 75954-71-1 (1E,3Z)-5-dimethylamino-7-methyl-1-phenylocta-1,3,7-triene 
• 75954-41-5 1-methyl-2-phenyl-1,2,3,6-tetrahydropyridine methiodide 
• 75954-70-0 dimethyl-(2-methylallyl)-<(2Z,4E)-5-phenylpenta-2,4-dienyl>ammonium chloride 
• 80988-38-1 (S)-(-)-1-methyl-2-phenylpiperidine 
• 144221-02-3 2-phenyl-6-(thiophen-2-yl)pyridine 
• 1030918-01-4 2-phenyl-6-(thiophen-3-yl)pyridine 
• 1146731-94-3 2-(4-nitrophenyl)-6-phenylpyridine 
• 273937-71-6 2-phenyl-6-(trifluoromethyl)pyridine 
• 36939-28-3 N-methyl-2-phenylpiperidine 

Relevant academic research and scientific papers

Influence of the anion nature and alkyl substituents in the behavior of ionic liquids derived from phenylpyridines

Quaternary alkyl 2-phenylpyridinium and 2-(2,4-difluorophenyl)pyridinium amines with iodide, hexafluorophosphate and bis(trifluoromethylsulfonyl)imide anions have been fully characterized by 1H NMR, FT-IR and MALDI mass spectroscopic methods an

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Synthesis of 2-Formylpyrroles from Pyridinium Iodide Salts

The first I2-mediated synthesis of 2-formylpyrroles from pyridinium salts is reported. This protocol enables the synthesis of diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The detailed mechanistic studies reveal that the reaction proceeds via a novel H2O-triggered ring opening of the pyridinium salt and a subsequent intramolecularly nucleophilic addition sequence.

Regioselective Direct C-H Trifluoromethylation of Pyridine

A highly efficient and regioselective direct C-H trifluoromethylation of pyridine based on an N-methylpyridine quaternary ammonium activation strategy has been developed. A variety of trifluoromethylpyridines can be obtained in good yield and excellent re

Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes

The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity. A plausible mechanism was proposed based on the Hammett study and KIE experiment.

Cation-π interactions secure aggregation induced emission of planar organic luminophores

The use of non-covalent intermolecular π+-π interactions between quaternary pyridinium or imidazolium cations and aromatic π systems is an efficient approach to achieve AIE in planar purely organic luminophores.

C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study

An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).

Asymmetric Hydrogenation of Pyridinium Salts with an Iridium Phosphole Catalyst

Iridium-catalyzed asymmetric hydrogenation of N-alkyl-2-alkylpyridinium salts provided 2-aryl-substituted piperidines with high levels of enantioselectivity. Simple benzyl and other alkyl groups successfully activated the challenging pyridine substrates toward hydrogenation. The use of the unusual chiral-phosphole-based MP2-SEGPHOS was the key to the success of this approach which provides a versatile and practical procedure for the synthesis of chiral piperidines. Ring to ring: Simple N-benzyl and N-alkyl groups successfully activated pyridine substrates toward hydrogenation. The use of the unusual chiral phosphole-based ligand L was the key to the success of this approach, which provides a versatile and practical procedure for the synthesis of chiral piperidines. cod=1,5-cyclooctadiene.

Stille reaction on pyridinium cations

A novel unit based on pyridinium cations has been synthesized by the Stille reaction and represents a model for development of molecular electronic devices.

From bipyridines to tobacco alkaloids and related compounds

Starting from structural considerations which led to the hypothesis that a chemical relationship could exist between two families of natural compounds (mainly pyridinic and pyrrolidinic alkaloids), experiments were carried out in order to establish a correlation route between the two studied classes. Of special interest was the central position of nicotine in these studies, and the main part of this work was devoted to the synthesis of nicotine starting from bipyridines. It was thus necessary to determine the conditions for selective reactions on one aromatic ring of bipyridines (N-methylation, N-oxidation and reduction of the heterocycle). Ring contraction procedure allowed us to obtain nicotine from the parent compound (3,3′-bipyridine). Complementary studies yielded various isomers of piperidinylpyridines (hexahydro derivatives of bipyridines) in a regiochemically controlled manner by means of original methods. Elsevier,.