71216-20-1

Basic information

• Product Name: 5-Bromo-2-mercaptobenzothiazole
• Synonyms: 2-METCAPTO-5-CHLORO-BENZOTHIAZOLE;2-MERCAPTO-5-CHLOROBENZOXAZOLE;5-Bromo-2-mercaptobenzothiazole;5-CHLORO-BENZOTHIAZOLE-2-THIOL;5-CHLORO-1,3-BENZOTHIAZOLE-2-THIOL;TIMTEC-BB SBB005398;5-BROMO-2-MERCAPTO BENZOTHLAZOLE;5-Bromo-2-Thiobenzothiazole
• CAS NO: 71216-20-1
• Molecular Formula: C₇H₄BrNS₂
• Molecular Weight: 246.15
• EINECS: 226-235-0
• Product Categories: Heterocycles;Heterocyclic Compound
• Mol File: 71216-20-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 198-200 °C(lit.)
• Boiling Point: 351.2ºC at 760 mmHg
• Flash Point: 166.2 ºC
• Appearance: /
• Density: 1.93 g/cm³
• Vapor Pressure: 4.17E-05mmHg at 25°C
• Refractive Index: 1.827
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Bromo-2-mercaptobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-mercaptobenzothiazole(71216-20-1)
• EPA Substance Registry System: 5-Bromo-2-mercaptobenzothiazole(71216-20-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22
• WGK Germany: 3
• RTECS: DL6490000
• Hazardous Substances Data: 71216-20-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C7H4BrNS2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

Upstream product

• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 2924-09-6 5-bromo-2-fluoroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 60811-17-8 5-bromo-2-chloroaniline 
• 140-92-1 potassium isopropylxanthate 
• 768-11-6 5-bromo-benzthiazole 
• 3638-73-1 2,5-dibromoaniline 

Downstream Products

• 203395-29-3 5-bromo-2-methylsulfanyl-1,3-benzothiazole 

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.

Preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as mercapto source

The invention belongs to the synthesis field of medicine chemical intermediate, and provides a preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as a mercapto source. According to the preparation method, under inert gas protection, in dimethyl sulphoxide solvent, substituted benzoxazole(thiazole) and 1,3-dimercaptopropane are subjected to 120 to 140 DEG Cheating stirring in the presence of an alkali, after 12 to 24h of reaction, an obtained reaction solution is cooled to room temperature, and is subjected to acidifying post-treatment so as to obtaina product. The reaction conditions are simple; function group compatibility is excellent; yield is relatively high; the obtained 2-mercaptobenzoxazole(thiazole) compounds are important organic synthesis intermediates; application range in the field of chemical raw material, pesticide, and medicine is wide; and practical value and social and economic benefit are excellent.