Ethyl picolinate

Base Information

• Chemical Name: Ethyl picolinate
• CAS No.: 2524-52-9
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE clear to slightly yellow liquid
• European Community (EC) Number: 219-758-0
• NSC Number: 31651,959
• UNII: RW5EU98AZQ
• DSSTox Substance ID: DTXSID9062489
• Nikkaji Number: J27.973K
• Wikidata: Q72476806
• ChEMBL ID: CHEMBL2251607
• Mol file: 2524-52-9.mol

Synonyms:ethyl picolinate

Chemical Property of Ethyl picolinate

Chemical Property:

• Appearance/Colour: clear yellowish or pink liquid
• Vapor Pressure: 0.0316mmHg at 25°C
• Melting Point: 2 °C(lit.)
• Refractive Index: 1.511
• Boiling Point: 243.7 °C at 760 mmHg
• PKA: 1.83±0.10(Predicted)
• Flash Point: 107.2 °C
• PSA: 39.19000
• Density: 1.102 g/cm³
• LogP: 1.25830
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: miscible
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

>＝98% ^*data from raw suppliers

PicolinicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CC=CC=N1
• Uses: Ethyl picolinate can be used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes. Ethyl picolinate is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors which is used in the treatment of diabetes. It is also used as pharmaceutical intermediate.

Technology Process of Ethyl picolinate

There total 53 articles about Ethyl picolinate 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%

2-Picolinic acid (98-98-6) + ethanol (64-17-5) → ethyl-2-picolinate (2524-52-9,1228273-66-2)

Guidance literature:

With sulfuric acid; at 70 ℃;

DOI:10.1002/cmdc.202100265

Reference yield: 96.0%

benzyl cis-3-[(tert-butoxycarbonyl)(pyridine-2-carbonyl)amino]-5-[4-(methoxycarbonyl)phenyl]piperidine-1-carboxylate → ethyl-2-picolinate (2524-52-9,1228273-66-2) + benzyl cis-3-[(tert-butoxycarbonyl)amino]-5-[4-(methoxycarbonyl)phenyl]piperidine-1-carboxylate

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In ethanol; toluene; at 80 ℃; for 15h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/acs.joc.9b02299

Reference yield: 94.0%

6-ethyl 1-methyl(2S,3R)-3-tert-butoxy-2-[(tert-butoxycarbonyl)-(pyridine-2-carbonyl)amino]hexanedioate → ethyl-2-picolinate (2524-52-9,1228273-66-2) + 6-ethyl 1-methyl (2S,3R)-3-tert-butoxy-2-[(tert-butoxycarbonyl)-amino]hexanedioate

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In ethanol; toluene; at 80 ℃; for 15h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/acs.joc.9b02299

upstream raw materials:

2-Cyanopyridine

2-Picolinic acid

ethanol

ethyl iodide

Downstream raw materials:

1,2-di(pyridin-2-yl)ethanone

α-<(2-pyridinyl)carbonyl>-γ-butyrolactone

pyridin-2-yl(pyridin-4-yl)methanone

2,2'-dipyridyl ketone

Refernces

• 1、 Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi. "Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker". . . Retrieved 2021/05/17.
• 2、 Baud, Damien,Bebrone, Carine,Becker, Katja,Benvenuti, Manuela,Cerboni, Giulia,Chelini, Giulia,Cutolo, Giuliano,De Luca, Filomena,Docquier, Jean-Denis,Feller, Georges,Fischer, Marina,Galleni, Moreno,Gavara, Laurent,Gresh, Nohad,Kwapien, Karolina,Legru, Alice,Mangani, Stefano,Mercuri, Paola,Pozzi, Cecilia,Sannio, Filomena,Sevaille, Laurent,Tanfoni, Silvia,Verdirosa, Federica,Berthomieu, Dorothée,Bestgen, Beno?t,Frère, Jean-Marie,Hernandez, Jean-Fran?ois. "4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors". supporting information. . Retrieved 2020/09/16.