5448-05-5

Basic information

• Product Name: diethyl 4-(4-methoxyphenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylate
• Synonyms: diethyl 4-(4-methoxyphenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylate
• CAS NO: 5448-05-5
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.4
• Mol File: 5448-05-5.mol
• Article Data: 101

Chemical Properties

• Melting Point: 50 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 451.4°Cat760mmHg
• Flash Point: 226.8°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 2.45E-08mmHg at 25°C
• Refractive Index: 1.538
• PKA: 3.41±0.28(Predicted)
• CAS DataBase Reference: diethyl 4-(4-methoxyphenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 4-(4-methoxyphenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylate(5448-05-5)
• EPA Substance Registry System: diethyl 4-(4-methoxyphenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylate(5448-05-5)

Safety Data

• Hazardous Substances Data: 5448-05-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H23NO5/c1-6-25-19(22)16-12(3)21-13(4)17(20(23)26-7-2)18(16)14-8-10-15(24-5)11-9-14/h8-11H,6-7H2,1-5H3

Upstream product

• 26456-05-3 10-methylacridinium perchlorate 
• 631-61-8 ammonium acetate 
• 141-97-9 ethyl acetoacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 626-34-6 ethyl aminocrotonate 
• 34014-60-3 diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methoxyphenyl)pyridine-3,5-dicarboxylate 

Downstream Products

• 42455-41-4 4-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 99001-90-8 4-(4-methoxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid monoethyl ester 
• 88752-75-4 4-(4-methoxy-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid 
• 629628-27-9 4-(4-methoxy-phenyl)-2,6-dimethyl-nicotinic acid ethyl ester 
• 847032-46-6 4-(4-methoxy-phenyl)-2,6-dimethyl-nicotinic acid 

Relevant articles and documents

Photocatalytic Hydrogen Production from Hantzsch 1,4-Dihydropyridines by Platinum(II) Terpyridyl Complexes in Homogeneous Solution

1,4-Dihydropyridines have been photocatalytically oxidized to pyridines by platinum(II) terpyridyl complexes with the generation of hydrogen in homogeneous solution. The hydrogen production proceeds in quantitative yield and with great catalytic turnover. Copyright

Superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF as efficient catalyst for oxidation of 1,4-dihydropyridines using hydrogen peroxide

A facile and efficient method was described for oxidation of some 3,5-diacyl or 3,5-diester 1,4-dihydropyridines using H2O2 in the presence of superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF. The Fe3O4@Ni-MOF has been obtained by Step-by-Step method in which magnetic Fe3O4 magnetic nanoparticles were coated with Ni-MOF using a mercaptoacetic acid linker. The synthesized catalyst was characterized using thermogravimetric analysis, FT-IR spectroscopy, powder X-ray diffraction, field emission scanning electron microscopy and energy-dispersive X-ray analysis. The novel superparamagnetic core-shell metal–organic framework Fe3O4@Ni-MOF revealed high efficiency for oxidation of various 1,4-dihydropyridines using hydrogen peroxide. The Box–Behnken design matrix and the response surface method were applied to investigate the optimization of the reaction conditions. The conditions for optimal reaction yield and time were: amount of catalyst ≈17 mmol, temperature ≈78°C and amount of hydrogen peroxide ≈ 1 ml. A variety of 3,5-diacyl or 3,5-diester 1,4-dihydropyridines with different substituted functional groups have been converted to corresponding pyridines with good to excellent isolated yields using H2O2 and Fe3O4@Ni-MOF. The catalyst was reused up to five times for the oxidation of 1,4-dihydropyridines without a significant loss in catalytic activity. The short reaction times, simplicity of method, good to excellent yields and reusability of catalyst were some advantages of the proposed procedure.

Trinuclear cis-dioxidomolybdenum(VI) complexes of compartmental C3 symmetric ligands: Synthesis, characterization, DFT study and catalytic application for hydropyridines (Hps) via the Hantzsch reaction

Trinuclear cis-dioxidomolybdenum(VI) complexes of the type [{MoVIO2(MeOH)}3L1-7] (1–7) have been synthesized using tris(H2ONO) donor ligands [H6L1-7 (I–VII)] assembled from benzene-1,3,5-tricarbohydrazide (bthz) and the corresponding salicylaldehyde (sal). All the ligands and the complexes were characterized by numerous techniques, such as FT-IR, UV–visible, NMR (1H and 13C) spectroscopy, electrochemical study, elemental analysis, thermogravimetric study and single crystal X-ray diffraction of the ligand III and complexes 1 and 5. In the presence of H2O2 as an oxidant, these complexes show excellent catalytic potential towards the one-pot three-components [ethyl acetoacetate, benzaldehyde (or its derivatives) and ammonium acetate] dynamic covalent assembly in the Hantzsch reaction. Under solvent free conditions, as high as 98% conversion along with 100% selectivity towards diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (1,4-DHP) has been achieved in 1 h. Although solvents do not improve the conversion, they do influence the selectivity of the products. With the elapse of time, the conversion of dihydropyridine to the diethyl 2,6-dimethyl-4-phenylpyridine-3,5-dicarboxylate derivative occurs and completes in ca. 10 h with a distinct color change, showing the importance of the catalysts. Efforts have been made to provide suitable reaction pathways for the catalytic reaction based on spectroscopic and density functional theory studies.