2116-64-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Phenethylpyridine serves as a crucial building block in the synthesis of an array of pharmaceuticals and agrochemicals. Its unique structure contributes to the development of new compounds with therapeutic or pesticidal properties, enhancing the range of available treatments and protections against pests.
Used as a Flavoring Agent in the Food Industry:
Beyond its applications in chemical synthesis, 4-Phenethylpyridine is also employed as a flavoring agent in food products. Its distinct aromatic profile adds a unique taste and scent to various consumables, contributing to the overall sensory experience of the food items.

InChI:InChI=1/C13H13N/c1-2-4-12(5-3-1)6-7-13-8-10-14-11-9-13/h1-5,8-11H,6-7H2

Upstream product

• 108-89-4 picoline 
• 100-44-7 benzyl chloride 
• 2785-29-7 benzyl potassium 
• 100-51-6 benzyl alcohol 
• 5097-93-8 trans-4-styrylpyride 
• 110-86-1 pyridine 
• 107264-16-4 diphenylmethanone O-(3-phenylpropanoyl) oxime 
• 3277-89-2 phenethylmagnesium bromide 
• 6844-47-9 4-[(trimethylsilanyl)methyl]-pyridine 
• 100-39-0 benzyl bromide 
• 768-90-1 1-Adamantyl bromide 
• 2502-99-0 (E)-4-(4-chlorostyryl)pyridine 
• 84355-17-9 1-(tert-Butyl-dimethyl-silanyl)-4-phenethyl-1,4-dihydro-pyridine 
• 100-43-6 4-vinylpyridine 

Downstream Products

• 110149-05-8 4-dibenzylmethylpyridine 
• 96428-84-1 2-amino-4-(2-phenylethyl)pyridine 
• 55-22-1 pyridine-4-carboxylic acid 
• 65-85-0 benzoic acid 
• 38025-43-3 1-benzyl-4-(2-phenylethyl)-1,2,3,6-tetrahydropyridine 
• 161772-58-3 Re(CO)3(C₁₂H₈N₂)(C₁₃H₁₃N)⁽¹⁺⁾*ClO₄^(1-) = [Re(CO)3(C₁₂H₈N₂)(C₁₃H₁₃N)]ClO₄ 
• 161772-56-1 Re(CO)3(C₁₀N₂H₈)C₅NH₄CH₂CH₂C₆H₅⁽¹⁺⁾*ClO₄^(1-)=Re(CO)3(C₁₀N₂H₈)C₅NH₄CH₂CH₂C₆H₅(ClO₄) 
• 127781-77-5 1-Methyl-4-(2-phenylethyl)-pyridiniumiodid 
• 1352558-67-8 4,4-bis(2-phenylethyl)piperidine-2,6-dicarbonitrile 
• 1352558-72-5 4,4-bis(2-phenylethyl)-1-triisopropylsilylpiperidine-cis-2,6-dicarbonitrile 
• 1352558-75-8 4,4-bis(2-phenylethyl)-1-triisopropylsilyl-1,2,3,4-tetrahydropyridine-2-carbonitrile 
• 1352558-78-1 1-acetyl-4,4-bis(2-phenylethyl)-1,2,3,4-tetrahydropyridine-2-carbonitrile 
• 1352558-81-6 4,4-bis(2-phenylethyl)piperidine-2-carbonitrile 
• 1352558-84-9 4,4-bis(2-phenylethyl)piperidine-2-carboxylic acid hydrochloride 

Relevant academic research and scientific papers

Catalytic reduction of an α,β-disubstituted alkene with sodium borohydride in the presence of tetra-tert-butylphthalocyanine complexes

Cobalt tetra-tert-butylphthalocyanine was found an efficient catalyst for the catalytic reduction of 4-[(E)-2-phenylethenyl]-pyridine to 4-(2-phenylethyl)pyridine with sodium borohydride.

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols

In this study, we developed a catalytic system for the C-alkylation of a methyl group on N-heteroaromatic compounds, including pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols based on a hydrogen-borrowing process with [Cp*IrCl2]2 (Cp*: η5-pentamethylcyclopentadienyl) combined with potassium t-butoxide and 18-crown-6-ether as the catalyst precursor.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.

Chemoselective Hydrogenation of Alkynes to (Z) -Alkenes Using an Air-Stable Base Metal Catalyst

A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperativity.

Lewis Acid-Catalyzed Selective Reductive Decarboxylative Pyridylation of N-Hydroxyphthalimide Esters: Synthesis of Congested Pyridine-Substituted Quaternary Carbons

A practical and efficient Lewis acid-catalyzed radical-radical coupling reaction of N-hydroxyphthalimide esters and 4-cyanopyridines with inexpensive bis(pinacolato)diboron as reductant has been developed. With ZnCl2 as the catalyst, a wide range of quaternary 4-substituted pyridines, including highly congested diarylmethyl and triarylmethyl substituents, could be selectively obtained in moderate to good yields with broad functional group tolerance. Combined theoretical calculations and experimental studies indicate that the Lewis acid could coordinate with the cyano group of the pyridine-boryl radical to lower the activation barrier of the C-C coupling pathway, leading to the formation of 4-substituted pyridines. Moreover, it could also facilitate the decyanation/aromatization of the radical-radical coupling intermediate.

Ni-catalyzed Reductive Deaminative Arylation at sp3 Carbon Centers

A Ni-catalyzed reductive deaminative arylation at unactivated sp3 carbon centers is described. This operationally simple and user-friendly protocol exhibits excellent chemoselectivity profile and broad substrate scope, thus complementing existing metal-catalyzed cross-coupling reactions to forge sp3 C-C linkages. These virtues have been assessed in the context of late-stage functionalization, hence providing a strategic advantage to reliably generate structure diversity with amine-containing drugs.

Semireduction of Alkynes Using Formic Acid with Reusable Pd-Catalysts

The treatment of PdCl2 with K2CO3 and HCO2H in dioxane gives black precipitates, which are an effective catalyst for the semireduction of alkynes to alkenes using formic acid as a reductant. Even 0.05 mol % Pd promoted the reduction reaction of tolane in high yield with high selectivity.

Ligand-Free RuCl3-Catalyzed Alkylation of Methylazaarenes with Alcohols

RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation, and hydrogenation reaction pathway.

Synthesis and utility of dihydropyridine boronic esters

When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.