3-chloro-pyridine-2,5-dicarboxylic acid diMethyl ester

Base Information

• Chemical Name: 3-chloro-pyridine-2,5-dicarboxylic acid diMethyl ester
• CAS No.: 106014-21-5
• Molecular Formula: C9H8ClNO4
• Molecular Weight: 229.61700
• Hs Code.: 2933399090
• Mol file: 106014-21-5.mol

Synonyms:dimethyl 3-chloro-2,5-pyridinedicarboxylate;2,5-Pyridinedicarboxylic acid,3-chloro-,dimethyl ester;3-chloro-pyridine-2,5-dicarboxylic acid dimethyl ester;

Chemical Property of 3-chloro-pyridine-2,5-dicarboxylic acid diMethyl ester

Chemical Property:

• Melting Point: 126.0-127.0 °C
• Boiling Point: 331.8±37.0 °C(Predicted)
• PKA: -2.94±0.10(Predicted)
• PSA: 65.49000
• Density: 1.347±0.06 g/cm3(Predicted)
• LogP: 1.30820
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

Dimethyl3-chloropyridine-2,5-dicarboxylate 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-chloro-pyridine-2,5-dicarboxylic acid diMethyl ester

There total 4 articles about 3-chloro-pyridine-2,5-dicarboxylic acid diMethyl ester 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: 81.2%

Pyridine-2,5-dicarboxylic acid N-oxide (32658-54-1) + methanol (67-56-1) → dimethyl 3-chloropyridine-2,5-dicarboxylate (106014-21-5)

Guidance literature:

Pyridine-2,5-dicarboxylic acid N-oxide; With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 65 ℃; for 2h;

methanol; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1021/ol0354369

Reference yield: 8.0%

methanol (67-56-1) + methyl 2,3-dichloro-pyridine-5-carboxylate (56055-54-0) + carbon monoxide (201230-82-2) → methyl 5-chloropyridine-3-carboxylate (51269-81-9) + methyl 5-chloro-6-methoxypyridine-3-carboxylate (220656-93-9) + dimethyl 3-chloropyridine-2,5-dicarboxylate (106014-21-5) + trimethyl pyridine-2,3,5-tricarboxylate

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium acetate; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; at 150 ℃; for 6h; under 11250.9 Torr; Further byproducts given;

DOI:10.1016/S0040-4020(98)01037-0

Reference yield:

Pyridine-2,5-dicarboxylic acid (100-26-5) → dimethyl 3-chloropyridine-2,5-dicarboxylate (106014-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / aq. Na₂WO₄; aq. H₂O₂ / 10 h / 80 - 85 °C

2.1: thionyl chloride / CH₂Cl₂; dimethylformamide / 2 h / 65 °C

2.2: 81.2 percent / CH₂Cl₂; dimethylformamide / 0 °C

With sodium tungstate; thionyl chloride; dihydrogen peroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0354369

upstream raw materials:

methanol

methyl 2,3-dichloro-pyridine-5-carboxylate

carbon monoxide

Pyridine-2,5-dicarboxylic acid N-oxide

Refernces

• 1、 -. "SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS". Page/Page column 111-112. . Retrieved 2009/04/25.
• 2、 -. "Process for preparing pyridinecarboxylic esters". . . Retrieved 2008/06/13.