615-22-5

Basic information

• Product Name: 2-Methylmercaptobenzothiazole
• Synonyms: LABOTEST-BB LT00460634;1-THIOMETHOXYBENZOTHIAZOLE;2-MERCAPTOBENZOTHIAZOLE METHYL ETHER;2-(METHYLTHIO)BENZOTHIAZOLE;2-METHYLMERCAPTOBENZOTHIAZOLE;2-(Methylsulfanyl)-1,3-benzothiazole;2-(methylthio)-benzothiazol;Benzothiazole, 2-(methylthio)-
• CAS NO: 615-22-5
• Molecular Formula: C₈H₇NS₂
• Molecular Weight: 181.28
• EINECS: 210-417-1
• Product Categories: BENZOTHIAZOLE;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 615-22-5.mol
• Article Data: 54

Chemical Properties

• Melting Point: 43-46 °C(lit.)
• Boiling Point: 177 °C / 22mmHg
• Flash Point: >230 °F
• Appearance: colorless to light yellow crystalline powder
• Density: 1.2625 (rough estimate)
• Vapor Pressure: 0.0014mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly, Sonicated)
• PKA: 1.22±0.10(Predicted)
• CAS DataBase Reference: 2-Methylmercaptobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylmercaptobenzothiazole(615-22-5)
• EPA Substance Registry System: 2-Methylmercaptobenzothiazole(615-22-5)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-15
• Safety Statements: 26-36-43
• WGK Germany: 3
• Hazardous Substances Data: 615-22-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 615-22-5 differently. You can refer to the following data:
1. 2-(Methylthio)Benzothiazole could be useful for removing pollutants in drinking water.
2. 2-(Methylthio)benzothiazole was used in trace determination of polar 1H-benzotriazoles and benzothiazoles in drinking and surface water by liquid chromatography-electrospray mass spectrometry.

Definition

ChEBI: An organic sulfide that is the methyl thioether of 1,3-benzothiazole-2-thiol.

General Description

2-(Methylthio)benzothiazole is the degradation product of 2-(thiocyanomethylthio)benzothiazole, a biocide used in the leather, pulp, paper and water-treatment industries.

Metabolic pathway

When 2-methylthiobenzothiazole and 35S-labeled glutathione (GSH) are incubated with rat liver microsomes, both 35S-labeled S-(2- benzothiazolyl)glutathione and 2- mercaptobenzothiazole are isolated from the reaction mixtures. Glutathione-S-transferase appears to be involved in the S-(2- benzothiazolyl)glutathione formation. Although sulfur is exchanged in this pathway, the net result of this pathway which involves oxidation of the methylthio group and GSH conjugation is an apparent S-demethylation of the methylthio group. Another S-demethylation pathway that does not involve GSH conjugation also functions in vitro.

InChI:InChI=1/C8H7NS2/c1-5-9-8-6(10)3-2-4-7(8)11-5/h2-4,10H,1H3

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 96-36-6 methyl phosphite 
• 26773-65-9 N-piperidin-2-benzothiazole sulfenamide 
• 32997-27-6 N-n-butyl-benzothiazolesulphenamide 
• 121-45-9 phosphorous acid trimethyl ester 
• 95-31-8 N-(tert-butyl)benzothiazole-2-sulfenamide 
• 66552-53-2 N-propyl-2-benzothiazolesulfenamide 
• 10220-34-5 N-isopropyl-2-benzothiazolesulfenamide 
• 17166-16-4 phosphorous acid tetramethyldiamide methylester 
• 27464-39-7 N,N-dimethyl-benzothiazolesulphenamide 
• 2801-21-0 benzothiazole sulfenamide 

Downstream Products

• 112577-41-0 (3-methyl-benzothiazol-2-yl)-(2-methyl-6-phenyl-pyridazin-3-yl)-methinium ; bromide 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 2254-94-6 3-methylbenzothiazole-2-thione 
• 60372-32-9 2-(cyclohexylthio)benzo[d]thiazole 
• 202002-02-6 3-cyclohexylbenzo[d]thiazole-2(3H)-thione 
• 23384-64-7 2-(benzo[d]thiazol-2-ylthio)-1-(p-tolyl)ethan-1-one 
• 106296-62-2 2-benzothiazol-2-ylthio(trimethylsilyl)ethanol 
• 112177-87-4 2-benzothiazol-2-ylthio-1,1-diphenylethanol 
• 79246-69-8 2,2a-Dihydro-2a-methylthio-1,2-diphenyl-1H-azeto<2,1-b>benzothiazol 
• 79246-70-1 trans-2,3-Dihydro-4-(methylthio)-2,3-diphenyl-1,5-benzothiazepin 
• 106296-74-6 2-benzothiazol-2-ylthio-1-(p-tolyl)ethanol 
• 93366-73-5 2-(phenethylthio)benzo[d]thiazole 
• 134792-08-8 α-<(benzothiazol-2-ylthio)methyl>-4-methoxybenzenemethanol 
• 27410-43-1 2-propylsulfanyl-benzothiazole 

Relevant articles and documents

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A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

RNA-targeting low-molecular-weight fluorophores for nucleoli staining: synthesis,in silicomodelling and cellular imaging

Herein we present our work on the synthesis, investigation of the photophysical properties, interactions with nucleic acids, molecular docking, and imaging application of three carbocyanine dyes. The described low-molecular-weight compounds were found to exhibit high resistance against photobleaching and showed promising optical properties as fluorescent labeling agents for ribonucleic acids. They form strong biocomplexes (log?Ks= 6.11-7.84) and revealed remarkable sensitivity towards RNA, reaching up to a 379 times increase of the emission signal when bound to AU-rich sequences. According to the score values obtained from the molecular docking studies, the compounds show strong binding affinity towards RNA macromolecules. All fluorophores exhibit significant cell tolerance since they were found to be 16 to 60 times less toxic against MRC5 cells (healthy human fibroblasts) compared to the conventional Thiazole Orange - TO. The IC50 concentrations for the compounds were calculated up to 40 μM in human fibroblasts MRC5, A549 adenocarcinomic human alveolar basal epithelial cells, the HCT116 human colon cancer cell line, and MDA-MB-231 adenocarcinoma cells. Analyzing the dyes for preferential cytotoxicity towards cancer cell lines in comparison to the normal human fibroblasts, we found a candidate exhibiting promising anticancer potential. Based on the selectivity (Si) towards cancer cells and more specifically against difficult to treat colon HCT116 carcinoma, we can suggest these small molecules as an interesting platform for further development. We have also demonstrated the efficiency of the carbocyanines as staining agents forin vivolabeling of human cells as well as microbial and eukaryotic cells.

Ag-Cu copromoted direct C2-H bond thiolation of azoles with Bunte salts as sulfur sources

A direct C2-H thiolation of azoles with Bunte salts was achieved under the combined action of copper and silver salts. This protocol could furnish various substituted 2-thioazoles in moderate to good yields. This method has a broad substrate scope and shows good functional group tolerance.