Methyl 2-chloro-6-methoxynicotinate

Base Information

• Chemical Name: Methyl 2-chloro-6-methoxynicotinate
• CAS No.: 95652-77-0
• Molecular Formula: C8H8 Cl N O3
• Molecular Weight: 201.609
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30442075
• Nikkaji Number: J1.403.924D
• Wikidata: Q82259151
• Mol file: 95652-77-0.mol

Synonyms:methyl 2-chloro-6-methoxynicotinate;95652-77-0;methyl 2-chloro-6-methoxypyridine-3-carboxylate;Methyl 2-chloro-6-methoxynicatinate;MFCD08275100;METHYL2-CHLORO-6-METHOXYNICOTINATE;SCHEMBL391203;DTXSID30442075;WDMMBHZPESWUCL-UHFFFAOYSA-N;AKOS005071481;AB44747;AD-0703;AC-29665;SY044995;AM20061643;CS-0040125;FT-0680807;A858965;J-521992;2-CHLORO-6-METHOXY-NICOTINIC ACID METHYL ESTER;2-Chloro-6-methoxy-3-pyridinecarboxylic acid methyl ester

Chemical Property of Methyl 2-chloro-6-methoxynicotinate

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 67-69°
• Refractive Index: 1.521
• Boiling Point: 276.793°C at 760 mmHg
• PKA: -1.13±0.10(Predicted)
• Flash Point: 121.2°C
• PSA: 48.42000
• Density: 1.288g/cm³
• LogP: 1.53020
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 201.0192708
• Heavy Atom Count: 13
• Complexity: 188

Purity/Quality:

98%min ^*data from raw suppliers

Methyl2-Chloro-6-methoxynicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=C(C=C1)C(=O)OC)Cl
• Uses: Methyl 2-Chloro-6-methoxynicotinate is used in preparation of Aryl-aniline and Heteroaryl-Aniline compounds useful in topical formulations for treatment of skin diseases.

Technology Process of Methyl 2-chloro-6-methoxynicotinate

There total 6 articles about Methyl 2-chloro-6-methoxynicotinate 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: 81.0%

methanol (67-56-1) + 2-chloro-6-methoxypyridine-3-carboxylic acid (503000-87-1) → methyl 2-chloro-6-methoxypyridine-3-carboxylate (95652-77-0)

Guidance literature:

2-chloro-6-methoxypyridine-3-carboxylic acid; With thionyl chloride; for 3h; Reflux;

methanol; for 3h; Reflux;

DOI:10.1021/acs.jmedchem.7b00596

Reference yield: 74.0%

2-chloro-6-methoxypyridine-3-carboxylic acid (503000-87-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-chloro-6-methoxypyridine-3-carboxylate (95652-77-0)

Guidance literature:

In methanol; diethyl ether; dichloromethane; at 0 - 20 ℃; for 0.666667h;

DOI:10.1002/ejoc.201300877

Reference yield: 47.0%

2-chloro-6-methoxypyridine-3-carboxylic acid (503000-87-1) + methyl iodide (74-88-4) → methyl 2-chloro-6-methoxypyridine-3-carboxylate (95652-77-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

upstream raw materials:

sodium methylate

methyl 2,6-dichloronicotinate

2-chloro-6-methoxypyridine-3-carboxylic acid

diazomethyl-trimethyl-silane

Downstream raw materials:

(2-chloro-6-methoxypyridin-3-yl)methanol

Refernces

• 1、 -. "INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION". Page/Page column 64. . Retrieved 2020/06/01.
• 2、 Zhao, Xue Zhi,Smith, Steven J.,Maskell, Daniel P.,Métifiot, Mathieu,Pye, Valerie E.,Fesen, Katherine,Marchand, Christophe,Pommier, Yves,Cherepanov, Peter,Hughes, Stephen H.,Burke, Terrence R.. "Structure-Guided Optimization of HIV Integrase Strand Transfer Inhibitors". . p. 7315 - 7332. Retrieved 2017/09/22.