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dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

27525-74-2

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27525-74-2 Usage

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 6033, 1993 DOI: 10.1016/S0040-4039(00)61720-3

Check Digit Verification of cas no

The CAS Registry Mumber 27525-74-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,5,2 and 5 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 27525-74:
(7*2)+(6*7)+(5*5)+(4*2)+(3*5)+(2*7)+(1*4)=122
122 % 10 = 2
So 27525-74-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO4/c1-6-8(10(13)15-3)5-9(7(2)12-6)11(14)16-4/h5H,1-4H3

27525-74-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate

1.2 Other means of identification

Product number -
Other names 3,5-pyridinedicarboxylic acid,2,6-dimethyl dimethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:27525-74-2 SDS

27525-74-2Relevant academic research and scientific papers

Light-Stimulated Generation of Free Radicals by Quinones-Chelators

Markova, Irina D.,Polyakov, Nikolay E.,Selyutina, Olga Yu.,Fedenok, Lidia G.,Fedotov, Kirill Yu.,Slepneva, Irina A.,Leshina, Tatyana V.,Pokrovsky, Andrey G.,Vasilieva, Nadezhda V.,Weiner, Lev M.

, p. 369 - 389 (2017)

The role of metal ions in the mechanism of light-stimulated redox activity of potential anticancer agent 2-phenyl-4-(butylamino)naphtha[2,3-h]quinoline-7,12-dione (Qc) has been studied by CIDNP (chemically induced dynamic nuclear polarization) and EPR methods. The photo-induced oxidation of NADH and its synthetic analog-substituted dihydropyridine (DHP)-by quinone Qc was used as a model. The Qc capability of producing chelating complexes with divalent metal ions of Fe, Zn and Ca was studied quantitatively by optical absorption spectroscopy. A significant decrease of electrochemical reduction potential of Qc (ΔE=0.4-0.6 eV for ACN and ACN/PBS solutions) in chelating complexes and in protonated form of Qc was observed. A pronounced increase in efficiency of DHP oxidation in chelating complexes with Zn2+ and Ca2+ ions compared with free Qc was demonstrated. The yields of free radicals, including reactive oxygen species (ROS) and reaction products, were a few times higher than those in the absence of metal ions. Application of such chelating compounds to enhance ROS generation looks very promising for anti-cancer therapy, including the photodynamic therapy.

Direct and co-catalytic oxidative aromatization of 1,4-dihydropyridines and related substrates using gold nanoparticles supported on carbon nanotubes

Prakash, Praveen,Gravel, Edmond,Li, Haiyan,Miserque, Frédéric,Habert, Aurélie,Den Hertog, Martien,Ling, Wai Li,Namboothiri, Irishi N. N.,Doris, Eric

, p. 6476 - 6479 (2016)

A heterogeneous catalyst was assembled by stabilization of gold nanoparticles on carbon nanotubes. The resulting nanohybrid was used in the catalytic aerobic oxidation of 1,4-dihydropyridines. The system proved very efficient on the investigated substrates either directly or in the presence of a quinone co-catalyst.

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

Janani, Marzieh,Senejani, Masumeh Abdoli,Isfahani, Tahereh Momeni

, (2021/07/21)

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.

Method for synthesizing pyridine and derivatives thereof by catalyzing Hanss ester 1, 4-dihydropyridine compound through titanocene dichloride

-

Paragraph 0013-0017; 0043-0047, (2021/07/28)

The invention discloses a method for synthesizing pyridine and derivatives thereof by catalyzing a Hass ester 1, 4-dihydropyridine compound through titanocene dichloride, the dihydropyridine structure of the Hass ester 1, 4-dihydropyridine compound has a certain aromatic ring driving force and is easily oxidized into a pyridine structure, and the the Hass ester 1, 4- dihydropyridine and the derivative thereof are subjected to oxidative conversion to generate the pyridine and the derivative thereof by taking titanocene dichloride as a catalyst, so that a simple way for preparing the pyridine and the derivative thereof is provided. The method is mild in reaction condition, simple to operate, short in reaction time, single in reaction product and high in atom economy, and only the product needs to be subjected to simple column chromatography separation after the reaction is finished. The Hanss ester 1, 4-dihydropyridine and the derivative thereof obtained by the invention have wide biological activity and medicinal value.

Transition-Metal-Free Alkylation and Acylation of Benzoxazinones with 1,4-Dihydropyridines

Byun, Youjung,Moon, Junghyea,An, Won,Mishra, Neeraj Kumar,Kim, Hyung Sik,Ghosh, Prithwish,Kim, In Su

, p. 12247 - 12256 (2021/09/07)

The direct functionalization of N-heterocycles is a vital transformation for the development of pharmaceuticals, functional materials, and other chemical entities. Herein, the transition-metal-free alkylation and acylation of C(sp2)-H bonds in biologically relevant 2-benzoxazinones with 1,4-dihydropyridines as readily accessible radical surrogates is described. Excellent functional group compatibility and a broad substrate scope were attained. Gram-scale reaction and transformations of the synthesized adducts via Suzuki coupling with heteroaryl boronic acids demonstrated the synthetic potential of the developed protocol.

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

Cao, Yue,Wu, Yong,Zhang, Yuanteng,Zhou, Jing,Xiao, Wei,Gu, Dong

, p. 3679 - 3686 (2021/06/18)

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Electrochemical Acceptorless Dehydrogenation of N-Heterocycles Utilizing TEMPO as Organo-Electrocatalyst

Wu, Yong,Yi, Hong,Lei, Aiwen

, p. 1192 - 1196 (2018/02/14)

Catalytic acceptorless dehydrogenation (CAD) has been a basically important organic transformation to ubiquitous unsaturated compounds without the usage of a sacrificial hydrogen acceptor. In this work, we successfully developed the first electrochemical acceptorless dehydrogenation (ECAD) of N-heterocycles using TEMPO as the organo-electrocatalyst. We have achieved the catalytic dehydrogenation of N-heterocycles in an anode and the release of H2 in a cathode using an undivided-cell system. A variety of six-membered and five-membered nitrogen-heteroarenes can be synthesized in good yields in this system. In addition, this protocol can also be used in the application of important molecular synthesis. Our electrochemical strategy provides a mild and metal-free route for (hetero)aromatic compounds synthesis via the CAD strategy.

One-pot synthesis of 3-hydroxy-2-oxindole-pyridine hybrids via Hantzsch ester formation, oxidative aromatization and sp3 C–H functionalization using FeWO4 nanoparticles as recyclable heterogeneous catalyst

Paplal, Banoth,Nagaraju, Sakkani,Sathish, Kota,Kashinath, Dhurke

, p. 110 - 115 (2017/10/16)

Synthesis of poly-substituted 3-hydroxy-2-oxindole-pyridine hybrids is reported via sp3 C–H bond functionalization as key steps using FeWO4 nanoparticles as reusable heterogeneous catalyst. Formation of Hantzsch ester (DHP) followed by aromatization, and sp3 C–H bond functionalization was achieved using FeWO4 nanoparticles (20 mol%) at 80 °C. Temperature dependent reactivity was observed for mono aldol (at 80 °C) and bis aldol (at 120 °C) products. The catalyst was regenerated and reused up to 6 cycles without losing catalytic activity. The FeWO4 nanoparticles were also used for oxidative aromatization of different DHP derivatives and for the sp3 C–H functionalization of 2-methyl pyridine.

Method for preparing 2,6-dialkyl-3,5-diester group symmetrical pyridine

-

Paragraph 0015; 0016; 0017; 0039; 0040; 0041; 0042-0083, (2018/04/03)

The invention discloses a method for preparing 2,6-dialkyl-3,5-diester group symmetrical pyridine. The method specifically comprises the following steps: with beta-keto ester as a reaction substrate,a metallic copper compound as a catalyst, a peroxide reagent as an oxidizing agent, ammonium acetate as a nitrogen source, and methanol as a carbon source (also serving as an organic solvent), performing methanol oxidation, dehydration condensation, nucleophilic addition and oxidative aromatization reaction, thereby obtaining the symmetrical 2,6-dialkyl-3,5-diester group symmetrical pyridine. Thepreparation method disclosed by the invention has the characteristics of readily available raw materials, cheap and lowly-toxic catalyst, high catalytic efficiency, simple convenient operation, environmental protection and the like.

Copper-Catalyzed Oxidative Coupling of β-Keto Esters with N-Methylamides for the Synthesis of Symmetrical 2,3,5,6-Tetrasubstituted Pyridines

Yan, Yizhe,Li, Hongyi,Li, Zheng,Niu, Bin,Shi, Miaomiao,Liu, Yanqi

, p. 8628 - 8633 (2017/08/23)

A copper-catalyzed oxidative formal [2+2+1+1] cycloaddition for the synthesis of symmetrical tetrasubstituted pyridines was first demonstrated. The reaction is involved in a domino cross-dehydrogenative coupling (CDC) of β-keto esters and N-methylamides, the C-N bond cleavage, the Michael addition, and a condensation and oxidative aromatization process. Multiple C-C and C-N bonds were constructed in one pot via the C-H and C-N cleavage of N-methylamides, which were employed as the carbon source of pyridines. The preliminary mechanistic studies revealed that the C(sp3)-H bond cleavage of N-methylamides was the rate-determining step.

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