Diethyl 4-bromopyridine-2,6-dicarboxylate

Base Information

• Chemical Name: Diethyl 4-bromopyridine-2,6-dicarboxylate
• CAS No.: 112776-83-7
• Molecular Formula: C11H12 Br N O4
• Molecular Weight: 302.125
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID80549644
• Nikkaji Number: J971.846J
• Wikidata: Q82428756
• Mol file: 112776-83-7.mol

Synonyms:Diethyl 4-bromopyridine-2,6-dicarboxylate;112776-83-7;2,6-Pyridinedicarboxylicacid, 4-bromo-, 2,6-diethyl ester;diethyl4-bromopyridine-2,6-dicarboxylate;diethyl 4-bromo-2,6-pyridinedicarboxylate;Diethyl-4-bromo-2,6-pyridinedicarboxylate;SCHEMBL841568;4-bromo-pyridine-2,6-dicarboxylic acid diethyl ester;DTXSID80549644;XZEHJCKDEUHHJY-UHFFFAOYSA-N;MFCD09910265;AKOS027382447;AS-70503;CS-0318792;E70480;J-400873;2,6-DIETHYL 4-BROMOPYRIDINE-2,6-DICARBOXYLATE

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 95-96 °C(Solv: isopropyl ether (108-20-3))
• Refractive Index: 1.537
• Boiling Point: 391.9°Cat760mmHg
• PKA: -2.14±0.10(Predicted)
• Flash Point: 190.8°C
• PSA: 65.49000
• Density: 1.455g/cm³
• LogP: 2.19750
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 300.99497
• Heavy Atom Count: 17
• Complexity: 259

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl 4-bromopyridine-2,6-dicarboxylate 95% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=CC(=N1)C(=O)OCC)Br

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

There total 14 articles about Diethyl 4-bromopyridine-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: 93.0%

Chelidamic acid (499-51-4) + ethanol (64-17-5) → diethyl 4-bromo-2,6-pyridinedicarboxylate (112776-83-7)

Guidance literature:

Chelidamic acid; With phosphorus pentabromide; In tetrachloromethane; for 12h; Reflux;

ethanol; In tetrachloromethane; at 80 ℃; for 0.5h;

DOI:10.1021/op020085j

Reference yield: 92.0%

4-hydroxypyridine-2,6-dicarboxylic acid diethylester (68631-52-7) → diethyl 4-bromo-2,6-pyridinedicarboxylate (112776-83-7)

Guidance literature:

4-hydroxypyridine-2,6-dicarboxylic acid diethylester; With phosphorus pentabromide; at 95 ℃; for 3.5h;

In ethanol; chloroform; at 0 ℃; for 3h;

DOI:10.1055/s-0034-1379549

Reference yield: 86.0%

4-oxo-1,4-dihydropyridine-2,6-diethylcarboxylate (115231-56-6) → diethyl 4-bromo-2,6-pyridinedicarboxylate (112776-83-7)

Guidance literature:

4-oxo-1,4-dihydropyridine-2,6-diethylcarboxylate; With phosphorus pentabromide; at 90 ℃; Inert atmosphere;

In ethanol; at 0 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/cjoc.201400213

upstream raw materials:

Chelidamic acid

ethanol

4-bromopyridine-2,6-dicarboxylic acid

4-bromopyridine-2,6-dicarbonyl dibromide

Downstream raw materials:

diethyl-2,6-pyridinedicarbonyl ester

3-(6-tert-butoxycarbonylamino-4-methylsulfanyl-pyridin-2-yl)-propionic acid

[4-methylsulfanyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

{6-[2-(1-methyl-2-oxo-butylcarbamoyl)-ethyl]-4-methylsulfanyl-pyridin-2-yl}-carbamic acid tert-butyl ester

Refernces

• 1、 Rizeq, Natalia,Georgiades, Savvas N.. "Linear and Branched Pyridyl-Oxazole Oligomers: Synthesis and Circular Dichroism Detectable Effect on c-Myc G-Quadruplex Helicity". . p. 122 - 131. Retrieved 2016.
• 2、 Rodrigues, Carime V.,Johnson, Katherine R.,Lombardi, Vincent C.,Rodrigues, Marcelo O.,Sobrinho, Josiane A.,De Bettencourt-Dias, Ana. "Photocytotoxicity of Thiophene- And Bithiophene-Dipicolinato Luminescent Lanthanide Complexes". . p. 7724 - 7734. Retrieved 2021.
• 3、 Martin, Adam D.,Britton, Joshua,Easun, Timothy L.,Blake, Alexander J.,Lewis, William,Schr?der, Martin. "Hirshfeld surface investigation of structure-directing interactions within dipicolinic acid derivatives". . p. 1697 - 1706. Retrieved 2015.
• 4、 Nettekoven, Matthias,Jenny, Christian. "The development of a practical and reliable large-scale synthesis of 2,6-diamino-4-bromopyridine". . p. 38 - 43. Retrieved 2003.
• 5、 Yigit, Mehmet V.,Cooper, Christopher G. F.,Wang, Yu,Moulton, Brian,MacDonald, John C.. "Reaction of 1,2-bis(2,6-dicarboxypyridin-4-yl)ethyne with Co(II) generates coordination monomers not polymers: Crystal structure of 4-(2,6- dicarboxypyridin-4-yl)ethynylpyridine-2,6-dicarboxylatotriaqua cobalt(II) monohydrate". . p. 371 - 379. Retrieved 2006.
• 6、 Wang, Yu,Cooper, Christopher G. F.,Luisi, Brian S.,Moulton, Brian,MacDonald, John C.. "Reaction of 1,2-bis(2,6-dicarboxypyridin-4-yl)ethyne and imidazole with Cu(II) generates a discrete complex not a coordination polymer: Crystal structure of [μ-4,4′-(1,2-ethynediyl)-bis(pyridine-2,6-dicarboxylato)- N, O, O′-μ-N′, O″, O″]-diaqua-bis(imidazole)- dicopper(II)". . p. 299 - 308. Retrieved 2007.
• 7、 Li, Qing-Feng,Du, Xiaodi,Jin, Lin,Hou, Mengmeng,Wang, Zhenling,Hao, Jianhua. "Highly luminescent hydrogels synthesized by covalent grafting of lanthanide complexes onto PNIPAM: Via one-pot free radical polymerization". . p. 3195 - 3201. Retrieved 2016.