Methyl 5-nitropicolinate

Base Information

• Chemical Name: Methyl 5-nitropicolinate
• CAS No.: 29682-14-2
• Molecular Formula: C7H6N2O4
• Molecular Weight: 182.136
• Hs Code.: 2933399090
• European Community (EC) Number: 800-855-7
• ChEMBL ID: CHEMBL2022009
• DSSTox Substance ID: DTXSID60499057
• Nikkaji Number: J149.536D
• Wikidata: Q82349515
• Mol file: 29682-14-2.mol

Synonyms:Methyl 5-nitropicolinate;29682-14-2;methyl 5-nitropyridine-2-carboxylate;Methyl 5-nitro-2-pyridinecarboxylate;2-Pyridinecarboxylic acid, 5-nitro-, methyl ester;MFCD09062740;5-nitro-pyridine-2-carboxylic acid methyl ester;SCHEMBL1403615;CHEMBL2022009;5-nitro-2-methoxycarbonylpyridine;DTXSID60499057;WBJDJRHSHXTRAT-UHFFFAOYSA-N;AMY10225;AKOS006330598;GS-5003;SB10169;SY150280;CS-0061867;FT-0705691;5-Nitro-2-pyridinecarboxylic acid methyl ester;EN300-129493;W17169;Z1198184840

Chemical Property of Methyl 5-nitropicolinate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 150-153 °C
• Refractive Index: 1.558
• Boiling Point: 340.18 °C at 760 mmHg
• PKA: -2.34±0.10(Predicted)
• Flash Point: 159.535 °C
• PSA: 85.01000
• Density: 1.376 g/cm³
• LogP: 1.29960
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 182.03275668
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-Nitropicolinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC=C(C=C1)[N+](=O)[O-]
• Uses: Methyl 5-Nitropicolinate is an intermediate used to prepare 5-thio-2-pyridinecarboxylic acid derivatives with antihypertensive activities.

Technology Process of Methyl 5-nitropicolinate

There total 4 articles about Methyl 5-nitropicolinate 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: 98.0%

methanol (67-56-1) + 5-nitropicolinic acid (30651-24-2) → 5-nitro-pyridine-2-carboxylic acid methyl ester (29682-14-2)

Guidance literature:

for 16h; Reflux;

Reference yield:

2-chloro-5-nitropyridine (4548-45-2) → 5-nitro-pyridine-2-carboxylic acid methyl ester (29682-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil

1.2: 2 h / Reflux

2.1: nitric acid / 15 h / Reflux

3.1: sulfuric acid / 5 h / Reflux

With sulfuric acid; nitric acid; sodium hydride; In tetrahydrofuran; mineral oil;

Reference yield:

1,3-diethyl 2-(5-nitropyridin-2-yl)propanedioate (60891-70-5) → 5-nitro-pyridine-2-carboxylic acid methyl ester (29682-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid / 15 h / Reflux

2: sulfuric acid / 5 h / Reflux

With sulfuric acid; nitric acid;

upstream raw materials:

methanol

5-nitropicolinic acid

1,3-diethyl 2-(5-nitropyridin-2-yl)propanedioate

2-chloro-5-nitropyridine

Downstream raw materials:

5-morpholinopicolinic acid

5-nitro-2-pyridinecarbaldehyde

5-fluoro-pyridine-2-carboxylic acid methyl ester

5-(m-chloro-benzylmercapto)-2-pyridinecarboxylic acid methyl ester

Refernces

• 1、 -. "As neuroprotective agents of pharmaceutical compounds". Paragraph 0299; 0300; 0305; 0306. . Retrieved 2019/06/26.
• 2、 -. "N2-PYRAZOLOSPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS". Page/Page column 29. . Retrieved 2011/06/16.