Chemical Properties
colorless to light yellow crystalline powder
Uses
2-(Methylthio)benzothiazole was used in trace determination of polar 1
H-benzotriazoles and benzothiazoles in drinking and surface water by liquid chromatography-electrospray mass spectrometry.
Uses
2-(Methylthio)Benzothiazole could be useful for removing pollutants in drinking water.
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.
Synthesis
16.7 g of
2-mercaptobenzothiazole was added to 100 ml of dichloromethane, 11.5 g of triethylamine was added, stirring to dissolve all the material, 13.1 g of dimethyl sulfate was added dropwise, after completion of dropwise addition stirring was carried out for 2 hrs at 45 degree C. TLC tracked the completion of the reaction, the reaction mixture was washed with water and evaporated to dryness. The residue was dissolved using 100 ml of anhydrous ethanol and crystallized by stirring at about 0 degree C. Benzothiazol-2-yl-methyl sulfide (I) precipitated as white crystals. It was filtered and dried in a vacuum oven to give 17.6 g of 2-methylthio benzothiazole.
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.
