40279-26-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Methylsulfanylquinoline is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs due to its unique chemical structure and properties.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-methylsulfanylquinoline is employed as a precursor in the production of agrochemicals, potentially enhancing crop protection and yield through its anti-bacterial and anti-fungal properties.
Used in Microbial Infection Treatment:
2-Methylsulfanylquinoline is considered for use as an anti-bacterial and anti-fungal agent, making it a promising candidate for the development of new drugs to combat microbial infections.
Used in Organic Electronic Devices:
Due to its semiconducting properties, 2-methylsulfanylquinoline has been studied for potential use in organic electronic devices, indicating its potential in advancing the field of materials science and technology.

InChI:InChI=1/C10H9NS/c1-12-10-7-6-8-4-2-3-5-9(8)11-10/h2-7H,1H3

Upstream product

• 2637-37-8 Quinoline-2-thiol 
• 77-78-1 dimethyl sulfate 
• 91-22-5 quinoline 
• 612-62-4 2-Chloroquinoline 
• 5188-07-8 sodium thiomethoxide 
• 623-51-8 ethyl 2-sulfanylacetate 
• 74-88-4 methyl iodide 
• 2637-37-8 Quinoline-2-thione 
• 529-23-7 o-aminobenzaldehyde 
• 349449-55-4 1,1-bis(ethylthio)-2-trimethylsilylethene 
• 67-56-1 methanol 
• 6560-83-4 2-iodoquinoline 
• 75-18-3 dimethylsulfide 
• 2005-43-8 2-bromoquinoline 

Downstream Products

• 55514-13-1 1-methyl-2-methylsulfanyl-quinolinium; toluene-4-sulfonate 
• 17075-19-3 2-(methylsulfonyl)quinoline 
• 104297-33-8 5-methyl-4-[2-(1-methyl-1H-[2]quinolylidene)-1-phenyl-ethylidene]-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 243-38-9 6H-quinindoline 
• 205-54-9 quinolino<1,2-a>benzimidazole 
• 877172-06-0 2-(2-bromo-4-methoxyanilino)quinoline 
• 877172-04-8 2-(2-bromo-4-methylanilino)quinoline 
• 877172-03-7 2-(2'-bromoanilino)quinoline 
• 62601-19-8 2-<(Chlormethyl)-thio>-chinolin 

Relevant academic research and scientific papers

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

Four-component coupling strategy for 2,3,4-trisubstituted 3,4-dihydroquinoline

- Trimethylsilyllithium attacked selectively at the 4-position of 2-(methylsulfanyl)quinoline. The lithium enamide intermediate generated in situ reacted with a series of electrophiles to introduce a substituent at the 3-position of the dihydroquinoline skeleton. Combined with the conversion of the 2-methylsulfanyl group to an aryl group via palladium-catalyzed Negishi-type coupling reaction, the net four-component coupling transformation in two steps provided a 2,3,4-trisubstituted 3,4-dihydroquinoline skeleton.

Cesium carbonate-promoted synthesis of aryl methyl sulfides using: S -methylisothiourea sulfate under transition-metal-free conditions

In the presence of cesium carbonate, an efficient synthesis of aryl methyl sulfides by the reactions of aryl halides with commercially available S-methylisothiourea sulfate is developed. This odourless and highly crystalline solid can be used as the subst

Chalcogen containing heterocyclic scaffolds: New hybrids with antitumoral activity

In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in order to determine their activity and selectivity against malignant cells. Ten compounds showed GI50values below 10?μM in at least one of the cancer cell lines and six of them exhibited a selectivity index higher than 9. In general, selenium-containing compounds were more active than their corresponding sulfur analogs but we found some thiocyanate derivatives with comparable or higher activity and selectivity. Among the different substituents, the seleno- and thio-cyanate groups showed the most promising results. On the basis of their potent activity and high selectivity index, compounds 7e and 8f (containing a thiocyanate and a selenocyanate group, respectively) were selected for further biological evaluation. Both the compounds induced caspase-dependent cell death and cell cycle arrest in G2/M phase. In addition, these compounds do not violate any of the Lipinski's Rule of Five and thus possess good potential to become drugs, compound 7e being particularly promising.

S-methylation of N-containing heterocyclic thiols with conjugated acids of methoxy groups

2-Mercaptopyridine-3-carboxylic acid reacts with methanol under acidic conditions to afford the corresponding S-methylated methyl ester, methyl 2-methylthiopyridine-2-carboxylate. Such S-methylation occurred for various N-containing heterocyclic thiols wi

Heteroannulation of 3-Bis(methylthio)acrolein with Aromatic Amines - A Convenient Highly Regioselective Synthesis of 2-(Methylthio)quinolines and their Benzo/Hetero Fused Analogs: A Modified Skraup Quinoline Synthesis

A simple and efficient synthesis of 2-(methylthio)quinolines and their condensed analogs has been developed through acid-induced cyclocondensation of their respective anilines or aromatic diamines with 3-bis(methylthio)acrolein. The 2-(methylthio) functionality in these quinolines could be either dethiomethylated or replaced by various nitrogen and carbon nucleophiles to afford 2-substituted quinolines.

One-Pot Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides

(Equation presented) The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S RN1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a one-pot two-step process for the synthesis of aromatic sulfur compounds.

Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation

Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation. This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process.

Lewis acid-promoted deoxygenative di[β,β-bis(ethylthio)]vinylation of aldehydes with trimethylsilylketene bis(ethylthio)acetal

Silylketene dithioacetal 1 reacted with aldehydes 2a-o, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3a-o, 15, or 5-phenyl-1,3,6-heptatriene 13b, in good to moderate yields. Similar reaction with 2-aminobenzaldehyde (16) or salicylaldehyde (17) produced quinoline 19 or chroman 20 in 40-58% yield. Treatment of 1 with α-diketones 22a-c or α-ketoester 24 led to tetrasubstituted furans 23a-c or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.

Aggregative activation in heterocyclic chemistry. Part 5. Lithiation of pyridine and quinoline with the complex base BuLi·Me2N(CH2)2OLi (BuLi·LiDMAE)

It is shown that the complex base BuLi·LiDMAE reacts with pyridine to give metallated species which, after trapping by electrophiles, lead to 2-substituted pyridines in good to excellent yields. The same reactions have been less successfully performed with quinoline.