Dimethyl 2,6-pyridinedicarboxylate

Base Information

• Chemical Name: Dimethyl 2,6-pyridinedicarboxylate
• CAS No.: 5453-67-8
• Molecular Formula: C9H9NO4
• Molecular Weight: 195.175
• Hs Code.: 29333990
• European Community (EC) Number: 226-697-3
• NSC Number: 18855
• UNII: YA2DJW5CFY
• DSSTox Substance ID: DTXSID40202940
• Nikkaji Number: J117.526B
• Wikidata: Q72471866
• ChEMBL ID: CHEMBL72405
• Mol file: 5453-67-8.mol

Synonyms:5453-67-8;dimethyl pyridine-2,6-dicarboxylate;Dimethyl 2,6-pyridinedicarboxylate;2,6-Pyridinedicarboxylic acid, dimethyl ester;Pyridine-2,6-dicarboxylic acid dimethyl ester;2,6-dimethyl pyridine-2,6-dicarboxylate;Dimethyl pyridine-2,6-carboxylate;2,6-Pyridinedicarboxylic Acid Dimethyl Ester;YA2DJW5CFY;MFCD00134493;CHEMBL72405;Dipicolinic Acid Dimethyl Ester;EINECS 226-697-3;NSC-18855;AI3-17592;2,6-Pyridinedicarboxylic acid, 2,6-dimethyl ester;Dimethyl Dipicolinate;DIMETHYLPYRIDINE-2,6-DICARBOXYLATE;UNII-YA2DJW5CFY;ChemDiv3_000174;2,6-Dicarbomethoxypyridine;Oprea1_104125;Oprea1_809421;SCHEMBL69653;2,6-Bismethoxycarbonylpyridine;F0771-0298;SNQQJEJPJMXYTR-UHFFFAOYSA-;DTXSID40202940;HMS1473H20;BCP32364;dimethyl 2,6-pyridine-dicarboxylate;NSC18855;AM1069;BDBM50403316;NSC 18855;STK720127;AKOS000265978;AB03744;AC-8949;CCG-103569;CS-W007966;IDI1_019492;NCGC00177691-01;Dimethyl 2,6-pyridinedicarboxylate, 99%;DS-11097;SY013899;A7918;FT-0635728;P1444;2,6-Pyridine dicarboxylic acid dimethyl ester;EN300-15507;SR-01000394135;SR-01000394135-1;Z25085939

Chemical Property of Dimethyl 2,6-pyridinedicarboxylate

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0.000293mmHg at 25°C
• Melting Point: 121-125 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 321.7 °C at 760 mmHg
• PKA: -0.46±0.10(Predicted)
• Flash Point: 148.3 °C
• PSA: 65.49000
• Density: 1.231 g/cm³
• LogP: 0.65480
• Storage Temp.: Refrigerator
• Solubility.: Chloroform
• Water Solubility.: Soluble in water(14 g/L) (25°C). Soluble in chloroform.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 195.05315777
• Heavy Atom Count: 14
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

2,6-Pyridinedicarboxylic acid dimethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC(=CC=C1)C(=O)OC
• General Description: Dimethyl 2,6-pyridinedicarboxylate is a key intermediate used in the synthesis of chiral macrocyclic pyridino-18-crown-6 ligands, where it participates in cyclization reactions to form diamido-substituted crown ethers. Its role is critical in constructing the pyridine-containing backbone of these macrocycles, which are subsequently evaluated for their enantiomeric recognition capabilities with chiral ammonium salts. DIMETHYL 2,6-PYRIDINEDICARBOXYLATE's structural features contribute to the overall conformation and binding properties of the resulting ligands, as evidenced by NMR and X-ray analyses in the study.

Technology Process of Dimethyl 2,6-pyridinedicarboxylate

There total 30 articles about Dimethyl 2,6-pyridinedicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + Pyridine-2,6-dicarboxylic acid (499-83-2) → 2,6-bis(methoxycarbonyl)pyridine (5453-67-8)

Guidance literature:

With thionyl chloride; for 3h; Heating;

DOI:10.1016/S0960-894X(02)01041-7

Reference yield: 93.0%

Pyridine-2,6-dicarboxylic acid (499-83-2) → 2,6-bis(methoxycarbonyl)pyridine (5453-67-8)

Guidance literature:

With methanol; thionyl chloride; for 16h; Reflux;

DOI:10.1016/j.tetlet.2012.12.095

Reference yield: 93.0%

Pyridine-2,6-dicarboxylic acid (499-83-2) + methyl iodide (74-88-4) → 2,6-bis(methoxycarbonyl)pyridine (5453-67-8)

Guidance literature:

Pyridine-2,6-dicarboxylic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.166667h;

methyl iodide; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1080/00397910802238809

upstream raw materials:

diazomethane

Pyridine-2,6-dicarboxylic acid

methanol

2,6-Pyridinedicarbonyl dichloride

Downstream raw materials:

pyridine-2,6-dicarbohydrazide

3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione

N-Fluoro-2,6-bis(methoxycarbonyl)pyridinium triflate

4,14-diphenyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione

Refernces

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands

10.1021/jo00046a020

The study focuses on the synthesis and characterization of eleven new chiral macrocycles (1-11) of the pyridino-18-crown-6 type. These compounds were prepared using various starting materials such as (S)-(+)-2-phenylglycine, formic acid, acetic anhydride, and diethylene glycol ditosylate, among others. The roles of these chemicals are crucial in the formation of the chiral diamines and glycols, which are then used to create the macrocyclic structures through cyclization reactions with compounds like dimethyl 2,6-pyridinedicarboxylate and O,O'-dimethyl 2,6-pyridinedicarbothioate. The study also investigates the enantiomeric recognition properties of these new chiral ligands with (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate using 'H NMR spectral techniques. The interactions and the degree of enantiomeric recognition are analyzed based on the differences in free energy of activation values (ΔG*) and log K values. Additionally, the X-ray analyses of the dithionoamido ligands (2, 6, and 8) reveal significant deviations of the S and N atoms from the plane of the pyridine ring, indicating structural distortions. The study provides insights into the factors influencing enantiomeric recognition and the potential applications of these chiral macrocycles in enantiomeric separations.