Methyl 6-(methylthio)nicotinate

Base Information

• Chemical Name: Methyl 6-(methylthio)nicotinate
• CAS No.: 74470-40-9
• Molecular Formula: C8H9NO2S
• Molecular Weight: 183.22800
• DSSTox Substance ID: DTXSID70358545
• Nikkaji Number: J2.118.954E
• Wikidata: Q82139177
• Mol file: 74470-40-9.mol

Synonyms:methyl 6-(methylthio)nicotinate;74470-40-9;methyl 6-methylsulfanylpyridine-3-carboxylate;3-Pyridinecarboxylic acid, 6-(methylthio)-, methyl ester;6-(methylthio)-3-pyridinecarboxylic acid methyl ester;SCHEMBL247044;DTXSID70358545;KMYTWSGXEHSNRY-UHFFFAOYSA-N;MFCD01928252;AKOS006280469;CS-0195619;FT-0620821;E89613;AJ-333/13050172

Chemical Property of Methyl 6-(methylthio)nicotinate

Chemical Property:

• PSA: 64.49000
• LogP: 1.59010
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.03539970
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl6-(methylthio)nicotinate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CN=C(C=C1)SC

Technology Process of Methyl 6-(methylthio)nicotinate

There total 6 articles about Methyl 6-(methylthio)nicotinate 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: 100.0%

6-Chloronicotinic acid methyl ester (73781-91-6) + sodium thiomethoxide (5188-07-8) → 2-methylthiopyridine-5-carboxylic acid methyl ester (74470-40-9)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; Cooling with ice;

Reference yield: 68.0%

methanol (67-56-1) + 6-Mercapto-nicotinic acid (17624-07-6,92823-43-3) → 2-methylthiopyridine-5-carboxylic acid methyl ester (74470-40-9)

Guidance literature:

With sulfuric acid; for 8h; Reflux;

DOI:10.3987/COM-09-11859

Reference yield: 53.0%

6-methylsulfanyl-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester → 2-methylthiopyridine-5-carboxylic acid methyl ester (74470-40-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2004.10.142

upstream raw materials:

6-Chloronicotinic acid methyl ester

sodium thiomethoxide

methanol

6-Mercapto-nicotinic acid

Downstream raw materials:

2-methylthiopyridine-5-carboxylic acid

(6-(methylthio)pyridin-3-yl)methanol

Refernces

• 1、 -. "HETEROCYCLIC FUSED PHENANTHROLINONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS". . . Retrieved 2012/01/06.
• 2、 Shimizu, Masao,Shimazaki, Teruaki,Kon, Yoshihiro,Konakahara, Takeo. "S-methylation of N-containing heterocyclic thiols with conjugated acids of methoxy groups". experimental part. p. 413 - 420. Retrieved 2010/09/05.