3622-23-9

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichlorobenzothiazole is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to be transformed into various derivatives with potential therapeutic applications. One such derivative is 6-chloro-2-(4-hydroxyphenoxy)benzothiazole, which may exhibit biological activities useful in the development of new drugs.
Used in Chemical Synthesis:
In the field of organic chemistry, 2,6-Dichlorobenzothiazole is used as a key building block for the creation of a wide range of chemical compounds. Its reactivity and stability make it a valuable component in the synthesis of various organic molecules, including those with potential applications in materials science, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, 2,6-Dichlorobenzothiazole is also utilized in research and development settings. It serves as a model compound for studying reaction mechanisms, exploring new synthetic routes, and testing the efficacy of various catalysts and reagents in organic reactions. This contributes to the advancement of chemical knowledge and the development of novel chemical processes.

InChI:InChI=1/C7H3Cl2NS/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H

Upstream product

• 95-24-9 6-chloro-2-aminobenzothiazole 
• 75-15-0 carbon disulfide 
• 106-47-8 4-chloro-aniline 
• 51011-54-2 6-chloro-2-hydrazinobenzothiazole 
• 51618-29-2 6-chloro-2-mercaptobenzothiazole 

Downstream Products

• 68194-99-0 [4-(6-chloro-benzothiazol-2-ylamino)-phenyl]-acetic acid 
• 62266-81-3 6-chloro-2,3-dihydrobenzothiazol-2-one 
• 948588-52-1 C₁₆H₁₅N₂OSCl 
• 63754-99-4 6-chloro-3-propyl-3H-benzothiazol-2-one 
• 63755-00-0 6-chloro-3-isopropyl-3H-benzothiazol-2-one 
• 30459-51-9 6-Chlor-3-ethylbenzothiazol-2-on 
• 63754-98-3 6-chloro-N-methyl-2(3H)-benzothiazolone 
• 58483-72-0 5-bromo-2-(6-chloro-benzothiazol-2-ylamino)-benzoic acid 
• 58483-73-1 4-bromo-2-(6-chloro-benzothiazol-2-ylamino)-benzoic acid 
• 791594-52-0 N-(4-iodo-2-fluorophenyl)-6-chloro-1,3-benzothiazol-2-amine 
• 374554-91-3 5-chloro-N-(6-chlorobenzothiazol-2-yl)-benzene-1,3-diamine 
• 140688-06-8 1-[6-Chloro-2-benzothiazolyl]-4,5-diphenyl-3-pyrazolidinone 
• 70216-88-5 4-(6-chloro-2-benzothiazolyl)-oxy-phenol 
• 51011-54-2 6-chloro-2-hydrazinobenzothiazole 

Relevant academic research and scientific papers

Preparation method of 2,6'-dichlorobenzothiazole

The invention discloses a preparation method of 2,6'-dichlorobenzothiazole, and belongs to the technical field of organic chemistry. The method comprises the following steps: using 2-amino-6-chlorobenzothiazole as a raw material and acetonitrile as a solvent, adding copper chloride and isoamyl nitrite, carrying out a reaction to form a mixture of 2,6'-dichlorobenzothiazole and other impurities, and carrying out column chromatography separation to obtain pure 2,6'-dichlorobenzothiazole at a yield of 45-66%. The preparation method makes up for the deficiency of existing synthesis processes, andprovides a new method for synthesizing the 2,6'-dichlorobenzothiazole.

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives

In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.

Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles

The 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazole scaffold was selected as a central core structure for the discovery of novel antibacterial compounds. A systematic variation of the substituents on the oxo-pyrazole moiety, as well as on the benzo moiety, led to the creation of a small and focused library of benzothiazoles that was subjected to antibacterial screening. In a first round of screening, activity of the compounds against six representative microorganisms was established. For the most potent congeners, MIC values against S. aureus and P. aeruginosa were determined. The structure-activity relationship study clearly revealed that subtle structural variations influence the antibacterial activity to a large extent. The most potent congeners displayed MIC values of 3.30 μM.

A mild and efficient one-pot synthesis of 2-aminated benzoxazoles and benzothiazoles

Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination-amination procedure is described. Compounds with a variety of substitution patterns are reported and the methodology has been successfully extended to benzothiazoles. Palladium catalysis on suitably activated examples has been employed to generate the desired compounds of interest.

Ferulic acid and benzothiazole dimer derivatives with high binding affinity to β-amyloid fibrils

New ferulic acid and benzothiazole dimer derivatives were synthesized and evaluated by in vitro competition assay using [125I]TZDM for their specific binding affinities to Aβ fibrils. In particular, 4a showed the most excellent binding affinity (Ki = 0.53 nM), compared to PIB (Ki = 0.77 nM), for benzothiazole binding sites of Aβ1-42 fibrils. This result suggests a possibility of a potential AD diagnostic probe for detection of Aβ fibrils.

Process for the manufacture of 2,6-dichlorobenzoxazole and 2,6-dichlorobenzthiazole

A process for the manufacture of 2,6-dichlorobenzoxazole and 2,6-dichlorobenzthiazole by chlorinating K+ or Na+ salts of 6-chloro-2-mercaptobenzoxazole or of 6-chloro-2-mercaptobenzthiazole in halogenated hydrocarbons as suspending agents.