Day: January 6, 2023

New Synthetic Routes to 3-, 5-, and 6-Aryl-2-chloropyridines was written by Church, Robert;Trust, Ronald;Albright, J. Donald;Powell, Dennis. And the article was included in Journal of Organic Chemistry in 1995.Application In Synthesis of 5-Phenylpyridin-2-ol This article mentions the following:

The efficient synthesis of 3-, 5-, and 6-aryl-2-chloropyridines, e.g., I (R¹ = H, 3-pyridinyl, SO₂Ph, etc., R² = H, 3-F₃CC₆H₄, 2,4-Cl₂C₆H₃, 4-Ph, etc., R³ = H, Ph, 3-pyridinyl, etc.), via the facile preparation of 5-(dimethyamino)aryl-substituted pentadienyl nitriles and cyclization with hydrochloric acid is described. This approach allows for the introduction of other electron-withdrawing substituents on the pyridine ring as well as the preparation of the desired unsubstituted arylpyridines. Some differences in the rates of cyclization of the pentadienyl nitriles as well as the yields of chloropyridines were observed that depended on the position and degree of substitution in the aryl substituent. The arylpentadienyl nitriles Me₂NCH:CCHCH:CArCN (Ar = 3-pyridinyl, 3-F₃CC₆H₄, 3-MeOC₆H₄, Ph) could also be converted directly into the corresponding 2-aminopyridines. In the experiment, the researchers used many compounds, for example, 5-Phenylpyridin-2-ol (cas: 76053-45-7Application In Synthesis of 5-Phenylpyridin-2-ol).

5-Phenylpyridin-2-ol (cas: 76053-45-7) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application In Synthesis of 5-Phenylpyridin-2-ol

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Advancing the Mechanistic Understanding of an Enantioselective Palladium-Catalyzed Alkene Difunctionalization Reaction was written by Jensen, Katrina H.;Webb, Jonathan D.;Sigman, Matthew S.. And the article was included in Journal of the American Chemical Society in 2010.Computed Properties of C13H15F3N2O This article mentions the following:

The mechanism of an enantioselective palladium-catalyzed alkene difunctionalization reaction has been investigated. Kinetic anal. provides evidence of turnover-limiting attack of a proposed quinone methide intermediate with MeOH and suggests that copper is involved in productive product formation, not just catalyst turnover. Through examination of substrate electronic effects, a Jaffe relationship was observed correlating rate to electronic perturbation at two positions of the substrate. Ligand effects were evaluated to provide evidence of rapid ligand exchange between palladium and copper as well as a correlation between ligand electronic nature and enantioselectivity. In the experiment, the researchers used many compounds, for example, (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2Computed Properties of C13H15F3N2O).

(S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Computed Properties of C13H15F3N2O

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Fluorescence “Turn On-Off” Sensing of Copper (II) Ions Utilizing Coumarin-Based Chemosensor: Experimental Study, Theoretical Calculation, Mineral and Drinking Water Analysis was written by Arslan, Fatma Nur;Geyik, Gonul Akin;Koran, Kenan;Ozen, Furkan;Aydin, Duygu;Elmas, Sukriye Nihan Karuk;Gorgulu, Ahmet Orhan;Yilmaz, Ibrahim. And the article was included in Journal of Fluorescence in 2020.COA of Formula: C5H6ClN This article mentions the following:

Abstract: Herein, we report the preparation of a fluorescent sensor based on coumarin derivative for copper (II) ion sensing in Acetonitrile/HEPES media. 6,7-dihydroxy-3-(4-(trifluoro)methylphenyl)coumarin (HMAC) sensor was fabricated and analyzed by spectroscopic techniques. The sensor demonstrates “turn on-off” fluorescence quenching in the presence of copper (II) ions at 458 nm. A clear complex between the chemosensor HMAC and copper (II) ions was characterized by ESI-MS as well as the Job′s method. Also, the limit of detection (LOD, 3σ/k) value was determined as 24.5 nM in Acetonitrile/HEPES (95/5, volum/volume) buffer media (pH = 7.0). This value is lower than the admissible level of copper (II) ions in drinking water (maximum 31.5 μM) reported by EU Water Framework Directive (WFD) and World Health Organization (WHO) guidelines. The theor. calculations (d. functional theory, DFT) have been performed for the geometric optimized structures. As a final stage, real sample analyses have successfully been performed by using 6,7-dihydroxy-3-(4-(trifluoro)methylphenyl)coumarin, as well as inductively coupled plasma optical emission spectroscopy method. The relative standard deviation for copper (II) in mineral and drinking water samples has been determined to be below 0.15% and recovery values are in the range of 95.48-109.20%. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7COA of Formula: C5H6ClN).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.COA of Formula: C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Safety Evaluation of the Copper-Mediated Cross-Coupling of 2-Bromopyridines with Ethyl Bromodifluoroacetate was written by Yang, Qiang;Cabrera, Pablo J.;Li, Xiaoyong;Sheng, Min;Wang, Nick X.. And the article was included in Organic Process Research & Development in 2018.COA of Formula: C6H3BrF3N This article mentions the following:

Potential safety hazards associated with Cu-mediated cross-coupling of 2-bromopyridines with Et bromodifluoroacetate were evaluated. An accelerating rate calorimetry thermal stability evaluation of the post-reaction mixture of 50.6 mmol 2-bromopyridine with 1.3 equivalent Et bromodifluoroacetate in the presence of 2.1 equivalent Cu in 40 mL DMSO indicated a significant decomposition event with a 115.5° onset temperature, which was significantly lower than that of neat DMSO. The reaction mixture in N,N-dimethylformamide did not display any exothermic decomposition up to 400° using differential scanning calorimetry. Reaction calorimetry evaluation of this reaction in DMSO showed a heat output (ΔH) of -13.5 kJ and an adiabatic temperature rise (ΔT_ad) of 129.5°, resulting in a maximum temperature of a synthesis reaction (MTSR) of 189.5°. The predicted heat of reaction using d. functional theory with BLYP functional agreed well with exptl. data. Scope studies with a multiple substituted 2-bromopyridines showed similar ΔH and ΔT_ad magnitudes vs. 2-bromopyridine when reacted at the same concentration In all studied cases, MTSR was significantly higher than the onset temperature of reaction mixture decomposition, indicating that in the absence of active cooling, the system could quickly trigger decomposition of the reaction mixture and result in a runaway reaction. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0COA of Formula: C6H3BrF3N).

2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. COA of Formula: C6H3BrF3N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Bio-derived 4-electron-accepting carbonyl-N-methylpyridinium species for high-performance lithium-organic batteries was written by Wang, Xiujuan;Xue, Wenhao;Gao, Guangyuan;Chen, Ling;Baumgartner, Thomas;He, Xiaoming. And the article was included in Cell Reports Physical Science in 2022.Quality Control of Phenyl(pyridin-2-yl)methanone This article mentions the following:

Structural diversity and low cost make organic materials ideal candidates for next-generation energy storage applications. To obtain high-performance electrode materials for lithium (Li)-organic batteries, the identification of suitable organic mols. that exhibit multiple and stable redox states, limited solubility, and improved conductivity is critical The leverage of bio-derived redox-active motifs holds great promise due to their built-in functionality and availability from natural resources. Here, we report the structural evolution from naturally occurring, two-electron accepting carbonylpyridinium units into four-electron accepting small organic mols. and their incorporation into high-performance polymers. Impressively, CP2-based electrode can read up to 807 mAh g^-1 after 300 cycles at a c.d. of 0.2 A g^-1. The superior battery performance rivals that of state-of-the-art Li-ion batteries and opens the door toward significantly broadening the impact of this critical energy-storage technol. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Quality Control of Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Quality Control of Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

N-oxidation of 2-substituted pyridines and quinolines by dimethyldioxirane: kinetics and steric effects was written by Winkeljohn, W. Rucks;Leggett-Robinson, Pamela;Peets, Monique R.;Strekowski, Lucjan;Vasquez, Pedro C.;Baumstark, A. L.. And the article was included in Heterocyclic Communications in 2007.Related Products of 644-98-4 This article mentions the following:

The oxidation of 2-substituted pyridines and selected N-containing aromatic heterocycles by dimethyldioxirane (1) produced the corresponding N-oxides as the sole products, quant. in most cases. The second order rate constants for N-oxidation by 1 in dried acetone at 23 °C were determined for 2-substituted pyridines 2-10, quinolines 11-14 and isoquinolines 15,16. An excellent correlation of log k₂ with Taft (σ^*) constants was obtained for 2-substituted pyridines (R = Me, Et, Prⁿ, Prⁱ, 3-pentyl) with the exception of the data for 2-t-butylpyridine. The results for the substituted quinolines and isoquinolines followed the same trends observed with the pyridines. Steric effects due to 2-substitution and peri-interactions can substantially reduce reactivity. The results provide insights into the geometrical requirements for N-oxidation by dimethyldioxirane. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Related Products of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Related Products of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Syntheses with the aid of (4-pyridylmethyl)lithium. I. Preparation of 4-alkylpyridines was written by Wibaut, J. P.;Hey, J. W.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1953.Category: pyridine-derivatives This article mentions the following:

PhLi in Et₂O slowly added to an equivalent amount of 4-methylpyridine (I) in Et₂O, and the mixture treated with an equivalent of alkyl bromide gives a 4-alkylpyridine as the main product. The following 4-alkylpyridines are obtained (alkyl, b.p., n²⁰_D, and m.p. of picrate given): Pr, b₂₀ 80°, 1.4966, 131°; Bu, b₂₀ 98°, 1.4937, 112.5°; C₅H₁₁, b₂₀ 114°, 1.4908, 104°; C₆H₁₃, b_0.1 68.5°, 1.4886, 93.5°; C₇H₁₅, b_0.1 80°, 1.4868, 89°; C₈H₁₇, b_0.1 91°, 1.4858, 88.5°; C₉H₁₉, b_0.1 103°, 1.4850, 104.5°; C₁₀H₂₁, b_0.1 115°, 1.4842, 112°. In the preparation of 4-butylpyridine, 60% of the desired product was obtained as well as 24% recovered I and 10% of a mixture of alkyl phenylpyridines. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Category: pyridine-derivatives).

4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Aerobic Oxidation of Pd^II to Pd^IV by Active Radical Reactants: Direct C-H Nitration and Acylation of Arenes via Oxygenation Process with Molecular Oxygen was written by Liang, Yu-Feng;Li, Xinyao;Wang, Xiaoyang;Yan, Yuepeng;Feng, Peng;Jiao, Ning. And the article was included in ACS Catalysis in 2015.Reference of 4783-68-0 This article mentions the following:

In the presence of Pd(OAc)₂, fused and unfused 2-arylpyridines and aryl-substituted nitrogen heterocycles, O-Me oximes of aryl ketones, and diaryl diazenes underwent regioselective aerobic nitration with tert-Bu nitrite and regioselective benzoylation with substituted toluenes in the presence of N-hydroxyphthalimide to yield nitroarenes and aryl ketones. The reactions are proposed to operate via a Pd(II)/Pd(IV) catalytic cycle. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Reference of 4783-68-0).

2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Reference of 4783-68-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of E-resveratrol in commercial scale production was written by Yang, Jie;Zhang, Ya-lu;Zhou, Zhi-xu;Sun, Tie-min. And the article was included in Zhongnan Yaoxue in 2015.SDS of cas: 628-13-7 This article mentions the following:

Objective: To study the synthesis of E-resveratrol from the view of com. scale production Methods: The target compound was prepared from 3,5-dihydroxy benzoic acid by methylation and reduction, followed by chloro-substituted and Arbuzov rearrangement reaction with tri-Et phosphate, then condensation with anisaldehyde and demethylation with pyridine hydrochloride. Results: The overall yield of this method was 52.0%. The purity of E-resveratrol was 98.54%. Conclusion: The improved procedure could be easily operated and was suitable for scale production In addition, the starting materials were conveniently obtained. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7SDS of cas: 628-13-7).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. SDS of cas: 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel indolizine compounds as potent inhibitors of phosphodiesterase IV (PDE4): structure-activity relationship was written by Chen, Shoujun;Xia, Zhiqiang;Nagai, Masazumi;Lu, Rongzhen;Kostik, Elena;Przewloka, Teresa;Song, Minghu;Chimmanamada, Dinesh;James, David;Zhang, Shijie;Jiang, Jun;Ono, Mitsunori;Koya, Keizo;Sun, Lijun. And the article was included in MedChemComm in 2011.Category: pyridine-derivatives This article mentions the following:

A series of novel indolizine 2-oxoacetamides were designed and synthesized as PDE4 inhibitors. Preliminary SAR of this new class of compounds revealed key structural features required for high potency. Compounds 1ab and 2a are among the most potent inhibitors of PDE4 with low single nM IC₅₀. Cellular activity was demonstrated by the inhibition of TNFα production from human PBMC with IC₅₀ ranging from 14 to 72 nM. Docking analyses suggest the OH group in 1ab enhance the binding via an H-bond interaction with the PDE4 enzyme. In the experiment, the researchers used many compounds, for example, 4-Methoxy-2-methylpyridine (cas: 24103-75-1Category: pyridine-derivatives).

4-Methoxy-2-methylpyridine (cas: 24103-75-1) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem