538-49-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Phenethenyl)pyridine is utilized as an active pharmaceutical ingredient for the development of various medications, leveraging its unique chemical properties to enhance therapeutic effects and improve patient outcomes.
Used in Flavor and Fragrance Industry:
As a flavoring agent, 2-(2-Phenethenyl)pyridine is employed to impart distinctive, floral notes to food products, contributing to the overall sensory experience of consumption.
Used in Fragrance Industry:
In the realm of fragrances, 2-(2-Phenethenyl)pyridine serves as a key ingredient to create complex and appealing scents for perfumes, colognes, and other personal care products, capitalizing on its strong floral aroma.
Used in Organic Synthesis:
2-(2-Phenethenyl)pyridine is used as a crucial intermediate in organic synthesis, particularly for the preparation of pyridine derivatives, which are essential components in a wide range of chemical and pharmaceutical applications.
Safety Considerations:
While 2-(2-Phenethenyl)pyridine is relatively stable under normal conditions, it is important to handle and store it with care to avoid potential irritation to the skin, eyes, and respiratory system. Proper safety measures should be implemented during its use to minimize health risks.

InChI:InChI=1/C13H11N/c1-2-6-12(7-3-1)9-10-13-8-4-5-11-14-13/h1-11H/b10-9+

Upstream product

• 109-06-8 α-picoline 
• 100-52-7 benzaldehyde 
• 6294-62-8 2-stilbazole dibromide 
• 120240-99-5 2-pyridyl styryl sulfoxide 
• 38700-15-1 triphenyl-(2-pyridylmethyl)phosphonium chloride 
• 1121-60-4 pyridine-2-carbaldehyde 
• 109-09-1 2-chloropyridine 
• 100-42-5 styrene 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 2294-74-8 1-phenyl-2-pyridin-2-yl-ethanol 
• 109-04-6 2-bromo-pyridine 
• 1008-89-5 2-phenylpyridine 
• 5029-67-4 2-iodopyridine 
• 100-69-6 2-vinylpyridine 

Downstream Products

• 1121-60-4 pyridine-2-carbaldehyde 
• 13474-48-1 1-phenyl-2-pyridin-2-yl-ethane-1,2-dione 
• 17152-06-6 2-(benzo[b]selenophen-2-yl)pyridine 
• 132363-97-4 2-(2-phenylethyl)piperidine 
• 60601-60-7 2-(2-cyclohexylethyl)-piperidine hydrochloride 
• 98-98-6 2-Picolinic acid 
• 65-85-0 benzoic acid 
• 100-52-7 benzaldehyde 
• 6294-62-8 2-stilbazole dibromide 
• 13141-42-9 2-(2-phenylethynyl)pyridine 
• 2116-62-3 2-(2-phenylethyl)pyridine 
• 2294-74-8 (-)-1-phenyl-2-(α-pyridyl)ethanol 
• 2294-74-8 (S)-1-phenyl-2-(pyridin-2-yl)ethan-1-ol 
• 1422450-72-3 2-[2-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]pyridine 

Relevant academic research and scientific papers

X-ray crystal structure of 2-styrylpyridine

We have crystallized the 2-styrylpyridine from the condensation reaction between the 2-methylpyridine with benzaldehyde in the formation of the model compound 2-styrylpyridine. The X-ray structure and NMR are currently reported. The main features of the structure is that it shows a localization of the double bonds rather than a delocalization of π electrons in an aromatic fashion.

A new insight into the push-pull effect of substituents via the stilbene-like model compounds

In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi

Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling–alkyne semi-hydrogenation reactions

A series of heterobimetallic PdII/MII complexes (MII = Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling–alkyne semi-hydrogenation reactions to form Z-aryl alkenes. The carbometalated heterobimetallic PdII/CoII complex CoPdL3′ demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH3·BH3 as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of Z-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.

Preparation method of alkyl/alkenyl substituted nitrogen-containing heterocyclic compound

The invention belongs to the technical field of organic synthesis, and particularly discloses a preparation method of an alkyl/alkenyl substituted nitrogen-containing heterocyclic compound, which comprises the following steps: (1) adding a 2-methyl nitrogen-containing heterocyclic compound, primary alcohol, alkali and an additive into an organic solvent, performing stirring reaction for 24 hours, and then cooling the product to room temperature; and (2) concentrating, separating and purifying the reaction liquid obtained in the step (1). The simple and effective method for preparing the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound under the metal-free and ligand-free conditions is realized, the 2-methyl nitrogen-containing heterocyclic compound and the primary alcohol which are economical and easy to obtain are used as raw materials, and the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound is prepared under the synergistic promotion of alkali and additives; and methyl alkylation and alkenylation reaction are carried out to generate the corresponding alkyl/alkenyl substituted nitrogen-containing heterocyclic compound. The product has high application value and can be used in the fields of spices, medicines, materials, organic synthesis and the like. The method is wide in application range, simple in process, green, simple, high in yield and suitable for popularization and application.

Role of Benzylic Deprotonation in Nickel-Catalyzed Benzylic Dehydrogenation

Alkylarenes are readily functionalized via the corresponding benzylic anions. Benzylic anions have been used for a range of catalytic reactions, including Ni-catalyzed dehydrogenation. Interestingly, the employment of Zn(TMP) 2for slow and incomplete deprotonation of the benzylic position was observed. This manuscript describes a preliminary investigation into the deprotonation of heteroarenes and its relationship to Ni-catalyzed benzylic dehydrogenation.

Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups

Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.

Structural Effect of Pincer Pd(II)–ONO Complexes Modified with Acylthiourea on Sizes of the In Situ Generated Pd Nanoparticles During Heck Coupling Reaction

Abstract: The Pd nanoparticles generated in situ from Pd–pincer complexes catalyzed Heck coupling reaction. For this purpose, new Pd(II)–ONO pincer complexes (1–4) containing acylthiourea ancillary ligand were obtained by treating [Pd(ONO)(CH3CN)] with the respective N-substituted carbamothioyl benzamide ligand (L1–L4). Formation of these complexes was confirmed by UV–Visible, FT-IR, NMR and mass spectroscopic techniques. The sizes of in situ formed Pd nanoparticles were greatly affected by the substituent in ancillary ligand, which in turn influenced their catalytic activity towards Heck coupling reaction. The in situ formed Pd nanoparticles during Heck reaction were removed from the reaction medium and analyzed using HR-TEM to estimate the sizes of the Pd nanoparticles. Complex [Pd(ONO)((N-benzylcarbamothioyl)benzamide)] (1) which does not possess any substituent on the benzyl moiety of acylthiourea produced the smallest Pd nanoparticles with the average particle size of 3.7?nm. Hence, complex 1 showed the utmost catalytic activity. With complex 1, 51–99% of conversion was observed during Heck coupling reaction of styrene with various aryl halides. XPS results confirmed that the recovered black particles were Pd(0). A reasonable recyclability results were achieved by these in situ generated Pd nanoparticles. Graphic Abstract: [Figure not available: see fulltext.]