Diethyl 2,6-pyridinedicarboxylate

Base Information

• Chemical Name: Diethyl 2,6-pyridinedicarboxylate
• CAS No.: 15658-60-3
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.229
• Hs Code.: 29333990
• European Community (EC) Number: 605-063-3
• NSC Number: 78907
• UNII: NS92Z2IS34
• DSSTox Substance ID: DTXSID50166100
• Nikkaji Number: J737.143H
• Wikidata: Q27285037
• ChEMBL ID: CHEMBL1741650
• Mol file: 15658-60-3.mol

Synonyms:diethyl pyridine-2,6-dicarboxylate;15658-60-3;Diethyl 2,6-pyridinedicarboxylate;Diethyl Dipicolinate;2,6-Pyridinedicarboxylic Acid Diethyl Ester;Dipicolinic Acid Diethyl Ester;2,6-diethyl pyridine-2,6-dicarboxylate;2,6-Dicarbethoxypyridine;NSC-78907;2,6-Pyridinedicarboxylic acid, 2,6-diethyl ester;2,6-Bis(ethoxycarbonyl)pyridine;MFCD00033792;UNII-NS92Z2IS34;MLS000084648;NS92Z2IS34;2,6-Pyridinedicarboxylic acid, diethyl ester;SMR000018996;Opera_ID_820;VANILLICACIDHYDRAZIDE;Oprea1_198544;Oprea1_663237;SCHEMBL1478915;CHEMBL1741650;KTOBUCHVPBPHMK-UHFFFAOYSA-;AMY9316;diethylpyridine-2,6-dicarboxylate;DTXSID50166100;HMS1607K13;HMS2332N11;NSC78907;STR08737;AKOS001483097;Diethyl 2,6-Pyridinedicarboxylic Acid;CCG-103096;CS-W010458;AC-30700;SY051286;TS-00541;EU-0033364;FT-0625288;P1240;EN300-117535;AB00404148-10;SR-01000388951;SR-01000388951-1;W-205803;Q27285037

Chemical Property of Diethyl 2,6-pyridinedicarboxylate

Chemical Property:

• Vapor Pressure: 5.43E-05mmHg at 25°C
• Melting Point: 44 °C
• Refractive Index: 1.508
• Boiling Point: 347.32 °C at 760 mmHg
• PKA: -0.20±0.10(Predicted)
• Flash Point: 163.853 °C
• PSA: 65.49000
• Density: 1.166 g/cm³
• LogP: 1.43500
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 230

Purity/Quality:

99%min ^*data from raw suppliers

Diethyl 2,6-Pyridinedicarboxylate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NC(=CC=C1)C(=O)OCC

Technology Process of Diethyl 2,6-pyridinedicarboxylate

There total 17 articles about Diethyl 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: 96.0%

Pyridine-2,6-dicarboxylic acid (499-83-2) + ethanol (64-17-5) → diethyl-2,6-pyridinedicarbonyl ester (15658-60-3)

Guidance literature:

With sulfuric acid; for 8h; Reflux;

DOI:10.1016/j.cclet.2020.03.053

Reference yield: 95.0%

tribromo-pyridine-2,6-dicarboxylic acid diethyl ester (205594-29-2) → diethyl-2,6-pyridinedicarbonyl ester (15658-60-3)

Guidance literature:

With hydrogen; potassium carbonate; palladium on activated charcoal; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1002/(SICI)1099-1344(199804)41:4<301::AID-JLCR81>3.0.CO;2-P

Reference yield: 95.0%

diethyl 4-bromo-2,6-pyridinedicarboxylate (112776-83-7) → diethyl-2,6-pyridinedicarbonyl ester (15658-60-3)

Guidance literature:

With hydrogen; potassium carbonate; palladium on activated charcoal; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/(SICI)1099-1344(199804)41:4<301::AID-JLCR81>3.0.CO;2-P

upstream raw materials:

2,6-Pyridinedicarbonyl dichloride

ethanol

Pyridine-2,6-dicarboxylic acid

2,6-dicarboethoxy-4-(1-phenyl-5-tetrazolyloxy)pyridine

Downstream raw materials:

2,6-Diacetylpyridine

2.6-bis(hydroxymethyl)pyridine

pyridine-2,6-dicarbohydrazide

ethyl 6-(hydroxymethyl)pyridine-2-carboxylate

Refernces

• 1、 Mueller. "-". . p. 336,338,339. Retrieved 1974.
• 2、 Kumar, Rakesh,Jain, Harshita,Gahlyan, Parveen,Joshi, Ankita,Ramachandran. "A highly sensitive pyridine-dicarbohydrazide based chemosensor for colorimetric recognition of Cu2+, AMP2-, F- and AcO- ions". . p. 8567 - 8576. Retrieved 2018.
• 3、 Li, Xiao,Zhan, Chuanlang,Wang, Yaobing,Yao, Jiannian. "Pyridine-imide oligomers". . p. 2444 - 2446. Retrieved 2008.
• 4、 Kadiyala, K. Ganesh,Tyagi, Tulika,Kakkar, Dipti,Chadha, Nidhi,Chuttani, Krishna,Roy, Bal Gangadhar,Thirumal, Meganathan,Mishra, Anil K.,Datta, Anupama. "Picolinic acid based acyclic bifunctional chelating agent and its methionine conjugate as potential SPECT imaging agents: Syntheses and preclinical evaluation". . p. 33963 - 33973. Retrieved 2015.
• 5、 Huang, Feng,Pei, Ying-Ying,Zuo, Hui-Hui,Chen, Jia-Liang,Yang, Yin,Su, Xun-Cheng. "Bioconjugation of proteins with a paramagnetic NMR and fluorescent tag". . p. 17141 - 17149. Retrieved 2013.
• 6、 McMillion, Noah D.,Wilson, Amanda W.,Goetz, McKenna K.,Chang, Mu-Chieh,Lin, Chia-Cheng,Feng, Wei-Jie,McCrory, Charles C. L.,Anderson, John S.. "Imidazole for Pyridine Substitution Leads to Enhanced Activity under Milder Conditions in Cobalt Water Oxidation Electrocatalysis". . p. 1391 - 1397. Retrieved 2019.
• 7、 -. "Metal organic complex with near-infrared absorption and emission properties and preparation method thereof". Paragraph 0110-0112. . Retrieved 2021/02/24.
• 8、 Joseph, M. Cassiem,Luckay, Robert C.,Nkabyo, Henry A.,Pearce, Brendan H.. "Pincer-like pyrazole- and imidazole-pyridinyl compounds: Synthesis, characterisation, crystallographic and computational investigation". . . Retrieved 2021/08/09.