Diethyl 4-chloropyridine-2,6-dicarboxylate

Base Information

• Chemical Name: Diethyl 4-chloropyridine-2,6-dicarboxylate
• CAS No.: 53389-01-8
• Molecular Formula: C11H12ClNO4
• Molecular Weight: 257.674
• Hs Code.: 2933399090
• European Community (EC) Number: 860-340-8
• NSC Number: 166604
• DSSTox Substance ID: DTXSID80304639
• Nikkaji Number: J578.807B
• Wikidata: Q63395946
• Mol file: 53389-01-8.mol

Synonyms:diethyl 4-chloropyridine-2,6-dicarboxylate;53389-01-8;Diethyl 4-chloro-2,6-pyridinedicarboxylate;2,6-Pyridinedicarboxylic acid, 4-chloro-, diethyl ester;2,6-diethyl 4-chloropyridine-2,6-dicarboxylate;NSC 166604;4-CHLORO-PYRIDINE-2,6-DICARBOXYLIC ACID DIETHYL ESTER;NSC166604;Oprea1_456782;4-Chloro-2,6-pyridinedicarboxylic acid diethyl ester;SCHEMBL3327719;AMY9314;DTXSID80304639;2,6-Pyridinedicarboxylic acid, 4-chloro-, 2,6-diethyl ester;MFCD00215521;STL290427;AKOS005070757;AB04877;NSC-166604;Diethyl 4-chloro-2,6-pyridine carboxylate;CS-0187359;FT-0680495;Diethyl 4-chloro-2,6-pyridinedicarboxylate #;EN300-97564;2,6-DIETHOXYCARBONYL-4-CHLORO-PYRIDINE;6F-911;A18857;D85985;J-400874;Q63395946

Chemical Property of Diethyl 4-chloropyridine-2,6-dicarboxylate

Chemical Property:

• Vapor Pressure: 6.26E-06mmHg at 25°C
• Melting Point: 91-93 °C
• Refractive Index: 1.522
• Boiling Point: 378.5 °C at 760 mmHg
• PKA: -2.14±0.10(Predicted)
• Flash Point: 182.7 °C
• PSA: 65.49000
• Density: 1.266 g/cm³
• LogP: 2.08840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 257.0454856
• Heavy Atom Count: 17
• Complexity: 259

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl 4-Chloropyridine-2,6-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=CC(=N1)C(=O)OCC)Cl
• Uses: Diethyl 4-Chloropyridine-2,6-dicarboxylate is a chemical reagent used in the synthesis of luminescent lanthanide complexes. Also used in the production of metal chelating inhibitors against fructose 1,6-bisphosphate (FBP) aldolase in the treatment of infectious bacteria and fungi.

Technology Process of Diethyl 4-chloropyridine-2,6-dicarboxylate

There total 6 articles about Diethyl 4-chloropyridine-2,6-dicarboxylate 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: 86.0%

Chelidamic acid (499-51-4) + ethanol (64-17-5) → diethyl 4-chloropyridine-2,6-dicarboxylate (53389-01-8)

Guidance literature:

Chelidamic acid; With trichlorophosphate; Heating / reflux;

ethanol; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

Reference yield: 76.0%

4-chloropyridine-2,6-dicarbonyl dichloride (71022-75-8) + ethanol (64-17-5) → diethyl 4-chloropyridine-2,6-dicarboxylate (53389-01-8)

Guidance literature:

at 20 ℃; for 1h;

DOI:10.1021/acs.inorgchem.9b03561

Reference yield:

Chelidamic acid (499-51-4) → diethyl 4-chloropyridine-2,6-dicarboxylate (53389-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / Heating

2: pyridine

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1016/j.bmcl.2005.07.055

upstream raw materials:

4-chloropyridine-2,6-dicarbonyl dichloride

ethanol

Chelidamic acid

chelidamic acid

Downstream raw materials:

4-chloro-2,6-pyridinedicarboxylic acid

dimethyl 4-methoxypyridine-2,6-dicarboxylate

(4-chloropyridine-2,6-diyl)bisdihydrazide

4-ethoxy-2,6-pyridinedicarboxylate d'ethyle

Refernces

• 1、 Johnson, Katherine R.,de Bettencourt-Dias, Ana. "Azido- and amino-substituted dipicolinates for the sensitization of the luminescent lanthanides EuIII and TbIII". . . Retrieved 2021.
• 2、 De Bettencourt-Dias, Ana,Fetto, Natalie R.,Monteiro, Jorge H. S. K.,Tucker, Matthew J.. "Luminescent Carbazole-Based EuIII and YbIII Complexes with a High Two-Photon Absorption Cross-Section Enable Viscosity Sensing in the Visible and near IR with One- And Two-Photon Excitation". supporting information. p. 3193 - 3199. Retrieved 2020/03/19.