Ethyl 4-chloropicolinate

Base Information

• Chemical Name: Ethyl 4-chloropicolinate
• CAS No.: 64064-56-8
• Molecular Formula: C8H8ClNO2
• Molecular Weight: 185.61
• Hs Code.: 2933399090
• European Community (EC) Number: 812-918-6
• DSSTox Substance ID: DTXSID20515247
• Wikidata: Q82376032
• Mol file: 64064-56-8.mol

Synonyms:Ethyl 4-chloropicolinate;64064-56-8;4-CHLOROPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER;ethyl 4-chloropyridine-2-carboxylate;MFCD09702465;ETHYL 4-CHLORO-2-PYRIDINECARBOXYLATE;4-chloro-pyridine-2-carboxylic acid ethyl ester;Ethyl4-chloropicolinate;SCHEMBL743661;AMY9345;DTXSID20515247;MXEIFGRJRCYUDJ-UHFFFAOYSA-N;ethyl 4-chloropyridin-2-carboxylate;CL0279;AKOS009115073;CS-W003624;MB07478;AS-11348;SY028389;FT-0725757;EN300-1252636;A834628;J-400953

Chemical Property of Ethyl 4-chloropicolinate

Chemical Property:

• Boiling Point: 278.561 °C at 760 mmHg
• PKA: -0.11±0.10(Predicted)
• Flash Point: 122.27 °C
• PSA: 39.19000
• Density: 1.246 g/cm³
• LogP: 1.91170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 185.0243562
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

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

Ethyl4-Chloropicolinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NC=CC(=C1)Cl
• Uses: Ethyl 4-Chloropicolinate is a reactant in the synthesis of 1,5-naphthyridine aminothiazole and pyrazole derivatives as potent and selective inhibitors of the transforming growth factor-β type I receptor, ALK5.

Technology Process of Ethyl 4-chloropicolinate

There total 8 articles about Ethyl 4-chloropicolinate 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: 90.0%

4-chloropicolinic acid (5470-22-4) + ethanol (64-17-5) → ethyl 4-chloropyridine-2-carboxylate (64064-56-8)

Guidance literature:

With sulfuric acid;

DOI:10.1016/j.bmcl.2005.02.084

Reference yield: 83.6%

ethanol (64-17-5) → ethyl 4-chloropyridine-2-carboxylate (64064-56-8)

Guidance literature:

4-chloropicolinic acid; With thionyl chloride; at 100 ℃; for 6h;

ethanol; at 0 - 20 ℃; for 25.5h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield: 80.2%

4-chloro-pyridine-2-carbonyl chloride (53750-66-6) + ethanol (64-17-5) → ethyl 4-chloropyridine-2-carboxylate (64064-56-8)

Guidance literature:

ethanol; With triethylamine; In dichloromethane; for 0.333333h; Cooling with ice;

4-chloro-pyridine-2-carbonyl chloride; In dichloromethane; for 0.5h; Cooling with ice;

upstream raw materials:

4-chloropicolinic acid

ethanol

4-chloro-pyridine-2-carbonyl chloride

4-chloro-2-pyridine carboxylic acid chloride hydrochloride

Downstream raw materials:

(4-chloropyridin-2-yl)methanol

4-(phenylthio)-2-picoynoylhydrazide

4-Phenylsulfanyl-pyridine-2-carbonyl azide

Refernces

• 1、 Xiong, Hehua,Cheng, Jianxin,Zhang, Jianqing,Zhang, Qian,Xiao, Zhen,Zhang, Han,Tang, Qidong,Zheng, Pengwu. "Design, synthesis, and biological evaluation of pyridineamide derivatives containing a 1,2,3-triazole fragment as type II c-Met Inhibitors". . . Retrieved 2020/01/13.
• 2、 -. "DIPHENYL DERIVATIVES AND USES THEREOF". Paragraph 1241. . Retrieved 2019/03/30.