80689-36-7

Usage

Synonyms

4,6-dimethyl-2-mercaptobenzothiazole or DM

Classification

Thiazole

Uses

Rubber accelerator and vulcanizing agent in rubber production

Function in rubber

Promotes cross-linking of rubber molecules, enhancing physical properties and performance

Additional applications

Synthesis of pharmaceuticals and agrochemicals

Safety concerns

Potential to cause skin and respiratory irritation, harmful if swallowed or inhaled

Upstream product

• 75-15-0 carbon disulfide 
• 95-68-1 2,4-Xylidine 
• 4102-54-9 2-iodo-4,6-dimethylaniline 
• 63133-82-4 2-chloro-4,6-dimethylaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Relevant academic research and scientific papers

Cleaner and greener synthesis of 3H-benzothiazole-2-thione and its derivatives

A cleaner and greener method of synthesis of 3H-benzothiazole-2-thione is being reported in this communication. In this method, various o-iodoaniline derivatives are reacted with carbon disulfide in the presence of Cs2CO3 and tetramethyl ammonium bromide (TMAB) to give 3H-benzothiazole-2-thione and its derivatives in higher yields.

LEGO-Inspired Drug Design: Unveiling a Class of Benzo[d]thiazoles Containing a 3,4-Dihydroxyphenyl Moiety as Plasma Membrane H+-ATPase Inhibitors

The fungal plasma membrane H+-ATPase (Pma1p) is a potential target for the discovery of new antifungal agents. Surprisingly, no structure–activity relationship studies for small molecules targeting Pma1p have been reported. Herein, we disclose a LEGO-inspired fragment assembly strategy for the design, synthesis, and discovery of benzo[d]thiazoles containing a 3,4-dihydroxyphenyl moiety as potential Pma1p inhibitors. A series of 2-(benzo[d]thiazol-2-ylthio)-1-(3,4-dihydroxyphenyl)ethanones was found to inhibit Pma1p, with the most potent IC50 value of 8 μm in an in vitro plasma membrane H+-ATPase assay. These compounds were also found to strongly inhibit the action of proton pumping when Pma1p was reconstituted into liposomes. 1-(3,4-Dihydroxyphenyl)-2-((6-(trifluoromethyl)benzo[d]thiazol-2-yl)thio)ethan-1-one (compound 38) showed inhibitory activities on the growth of Candida albicans and Saccharomyces cerevisiae, which could be correlated and substantiated with the ability to inhibit Pma1p in vitro.

Copper-Catalyzed Three-Component Synthesis of Benzothiazolethiones from o-Iodoanilines, Isocyanide, and Potassium Sulfide

An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.