1849-65-6

Basic information

• Product Name: 4-Chloro-2-mercaptobenzothiazole
• Synonyms: 2(3H)-Benzothiazolethione,4-chloro-(9CI);4-Chloro-2-mercaptobenzothiazole;4-Chloro-2(3H)-benzothiazolethione;4-Chloro-2-benzothiazolethiol;4-Chlorobenzo[d]thiazole-2-thiol;4-Chlor-benzthiazol-2-thiol
• CAS NO: 1849-65-6
• Molecular Formula: C₇H₄ClNS₂
• Molecular Weight: 201.7
• Product Categories: BENZOTHIAZOLE;Heterocycles;Heterocyclic Compound
• Mol File: 1849-65-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 209-210 °C
• Boiling Point: 329 °C
• Flash Point: 153 °C
• Appearance: /
• Density: 1.60
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.756
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.61±0.20(Predicted)
• CAS DataBase Reference: 4-Chloro-2-mercaptobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-mercaptobenzothiazole(1849-65-6)
• EPA Substance Registry System: 4-Chloro-2-mercaptobenzothiazole(1849-65-6)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 1849-65-6(Hazardous Substances Data)

Usage

General Description

4-Chloro-2-mercaptobenzothiazole is a chemical compound with the molecular formula C7H4ClNS2. It is a pale yellow powder that is primarily used as a corrosion inhibitor in metalworking fluids, such as cutting and grinding fluids. It is also used as a biocide in industrial water treatment and as a rubber accelerator in the production of rubber compounds. However, it is important to note that 4-Chloro-2-mercaptobenzothiazole is considered hazardous, as it is toxic if ingested, inhaled, or absorbed through the skin. It can also cause skin and eye irritation, and may have harmful effects on aquatic organisms. Therefore, proper safety measures and handling procedures should be followed when working with this chemical.

InChI:InChI=1/C7H4ClNS2/c8-4-2-1-3-5-6(4)9-7(10)11-5/h1-3H,(H,9,10)

Upstream product

• 140-92-1 potassium isopropylxanthate 
• 608-31-1 2,6-Dichloroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 3048-45-1 4-chloro-1,3-benzothiazole 

Downstream Products

• 39205-62-4 4-chlorobenzo[d]thiazol-2(3H)-one 
• 30986-63-1 2-(4-Chlorbenzothiazolylsulfonyl)thiomethylthiocyanat 
• 2942-09-8 7-chloro-1,3-benzothiazole 
• 3507-40-2 4-chloro-2-(methylsulfanyl)benzo[d]thiazole 
• 51769-38-1 (4-chloro-1,3-benzothiazol-2-yl)hydrazine 

Relevant articles and documents

Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

Limited therapeutic options are available for the treatment of human schistosomiasis caused by the parasitic Schistosoma flatworm. The B cell lymphoma-2 (BCL-2)-regulated apoptotic cell death pathway in schistosomes was recently characterized and shown to share similarities with the intrinsic apoptosis pathway in humans. Here, we exploit structural differences in the human and schistosome BCL-2 (sBCL-2) pro-survival proteins toward a novel treatment strategy for schistosomiasis. The benzothiazole hydrazone scaffold previously employed to target human BCL-XL was repurposed as a starting point to target sBCL-2. We utilized X-ray structural data to inform optimization and then applied a scaffold-hop strategy to identify the 5-carboxamide thiazole hydrazone scaffold (43) with potent sBCL-2 activity (IC50 30 nM). Human BCL-XL potency (IC50 13 nM) was inadvertently preserved during the optimization process. The lead analogues from this study exhibit on-target activity in model fibroblast cell lines dependent on either sBCL-2 or human BCL-XL for survival. Further optimization of the thiazole hydrazone class is required to exhibit activity in schistosomes and enhance the potential of this strategy for treating schistosomiasis.

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source

A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.

Analogues of the allosteric heat shock protein 70 (Hsp70) inhibitor, MKT-077, as anti-cancer agents

The rhodacyanine, MKT-077, has antiproliferative activity against cancer cell lines through its ability to inhibit members of the heat shock protein 70 (Hsp70) family of molecular chaperones. However, MKT-077 is rapidly metabolized, which limits its use as either a chemical probe or potential therapeutic. We report the synthesis and characterization of MKT-077 analogues designed for greater stability. The most potent molecules, such as 30 (JG-98), were at least 3-fold more active than MKT-077 against the breast cancer cell lines MDA-MB-231 and MCF-7 (EC50 values of 0.4 ± 0.03 and 0.7 ± 0.2 μM, respectively). The analogues modestly destabilized the chaperone clients, Akt1 and Raf1, and induced apoptosis in these cells. Further, the microsomal half-life of JG-98 was improved at least 7-fold (t1/2 = 37 min) compared to MKT-077 (t1/2 5 min). Finally, NMR titration experiments suggested that these analogues bind an allosteric site that is known to accommodate MKT-077. These studies advance MKT-077 analogues as chemical probes for studying Hsp70s roles in cancer.