3145-77-5

Basic information

• Product Name: 2-[(methylsulfanyl)methyl]pyridine
• CAS NO: 3145-77-5
• Molecular Formula: C₇H₉NS
• Molecular Weight: 139.2181
• Mol File: 3145-77-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 208.8°C at 760 mmHg
• Flash Point: 80.1°C
• Density: 1.075g/cm³
• Vapor Pressure: 0.303mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 2-[(methylsulfanyl)methyl]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(methylsulfanyl)methyl]pyridine(3145-77-5)
• EPA Substance Registry System: 2-[(methylsulfanyl)methyl]pyridine(3145-77-5)

Safety Data

• Hazardous Substances Data: 3145-77-5(Hazardous Substances Data)

Usage

Derived from

Pyridine

Methylsulfanyl group attachment

Second carbon of the pyridine ring

Usage

Synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Application

Building block in organic chemistry for the formation of various functionalized pyridines

Biological activities and pharmacological properties

Potential for various applications in the chemical and pharmaceutical industries

Upstream product

• 2044-73-7 2-(sulfanylmethyl)pyridine 
• 74-88-4 methyl iodide 
• 215035-91-9 pyridin-2-ylmethyl methanesulphonate 
• 5188-07-8 sodium thiomethoxide 
• 624-92-0 Dimethyldisulphide 
• 109-06-8 α-picoline 
• 586-98-1 2-Hydroxymethylpyridine 
• 75-18-3 dimethylsulfide 
• 107264-09-5 1-fluoro-pyridinium tetrafluoroborate 

Downstream Products

• 1224866-71-0 PdI(C₆H₄-4-NO₂)(PyCH₂SMe) 
• 958877-26-4 [Pd(2-methylthiomethylpyridine)(tolyl)I] 
• 958877-49-1 [Pd(2-methylthiomethylpyridine)(C(tolyl)N(CH₂tosyl))I] 
• 958877-40-2 [Pd(2-methylthiomethylpyridine)(C(tolyl)N(2,6-Me₂C₆H₃))I] 
• 958877-46-8 [Pd(2-methylthiomethylpyridine)(C(methyl)N(CH₂tosyl))I] 
• 958877-35-5 [Pd(2-methylthiomethylpyridine)(1-(2,6-dimethylphenylimino)ethyl)I] 
• 958877-45-7 [Pd(2-methylthiomethylpyridine)(C(methyl)N(CH₂tosyl))Cl] 
• 958877-34-4 [Pd(2-methylthiomethylpyridine)(1-(2,6-dimethylphenylimino)ethyl)Cl] 

Relevant articles and documents

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Sulfur as ligand atom in chelate complexes

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A study on the BF3-directed lithiation of 2-picoline and 2,3-lutidine

The lithiation of 2-picoline (1a) and 2,3-lutidine (1b) in diethyl ether has been investigated with and without prior complexation with BF3. The reactions of the BF3 adduct of these moieties (2a and 2b) with lithium diisopropylamide (LDA) and subsequent trapping with benzaldehyde or dimethyl disulfide gave products corresponding to exclusive lithiation at the α-methyl carbon. The yields obtained with these reactions were far superior to that obtained with the lithiation of uncomplexed 1a and 1b. The dilithiation of 2a and 2b has also been investigated and a convenient and efficient synthesis of the diiodo derivatives of 1,2-bis(pyridin-2-yl)ethane has been provided.

The methyl group as a source of structural diversity in heterocyclic chemistry: Side chain functionalization of picolines and related heterocycles

(Chemical Equation Presented) The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters.