Methyl 5-chloronicotinate

Base Information

• Chemical Name: Methyl 5-chloronicotinate
• CAS No.: 51269-81-9
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID10572627
• Wikidata: Q82461042
• Mol file: 51269-81-9.mol

Synonyms:Methyl 5-chloronicotinate;51269-81-9;5-CHLOROPYRIDINE-3-CARBOXYLIC ACID METHYL ESTER;methyl 5-chloropyridine-3-carboxylate;MFCD09702467;Methyl 3-chloropyridine-5-carboxylate;Methyl-5-chloro Nicotinate;Methyl5-chloronicotinate;3-Pyridinecarboxylic acid, 5-chloro-, methyl ester;SCHEMBL1436200;DTXSID10572627;TVUWLLCWQGXPSH-UHFFFAOYSA-N;5-chloro-nicotinic acid methyl ester;AKOS006331659;AS-18390;SY031553;AM20061815;CS-0019209;W11186;A871326;J-517412

Chemical Property of Methyl 5-chloronicotinate

Chemical Property:

• Vapor Pressure: 0.066mmHg at 25°C
• Melting Point: 88-90 °C
• Refractive Index: 1.531
• Boiling Point: 230.4 °C at 760 mmHg
• PKA: 0.91±0.20(Predicted)
• Flash Point: 93.1 °C
• PSA: 39.19000
• Density: 1.294 g/cm³
• LogP: 1.52160
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 171.0087061
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

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

Methyl5-Chloronicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=CN=C1)Cl

Technology Process of Methyl 5-chloronicotinate

There total 3 articles about Methyl 5-chloronicotinate 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: 80.0%

methanol (67-56-1) + 5-chloronicotinic acid (22620-27-5) → methyl 5-chloropyridine-3-carboxylate (51269-81-9)

Guidance literature:

With sulfuric acid; at 75 ℃; for 12h;

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:

→ methyl 5-chloropyridine-3-carboxylate (51269-81-9)

Guidance literature:

3-Carbomethoxypyridin-1-oxid, N-Phenylbenzimidoylchlorid;

DOI:10.1021/jo00927a002

upstream raw materials:

methanol

5-chloronicotinic acid

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

carbon monoxide

Downstream raw materials:

5-chloropyridine-3-carbohydrazide

(E)-5-chloro-N'-(1-(5-chloro-2-hydroxyphenyl)ethylidene)nicotinohydrazide

(5-chloro-pyridin-3-yl)-methanol

Refernces

• 1、 -. "BENZENE SULFONAMIDES AS CCR9 INHIBITORS". Page/Page column 100. . Retrieved 2015/07/15.
• 2、 Sorna, Venkataswamy,Theisen, Emily R.,Stephens, Bret,Warner, Steven L.,Bearss, David J.,Vankayalapati, Hariprasad,Sharma, Sunil. "High-throughput virtual screening identifies novel N ′-(1- phenylethylidene)-benzohydrazides as potent, specific, and reversible LSD1 inhibitors". . p. 9496 - 9508. Retrieved 2014/01/06.