154327-24-9

Basic information

• Product Name: 4-Fluoro-2(3H)-Benzothiazolethione
• Synonyms: 4-Fluoro-2(3H)-Benzothiazolethione;4-Fluoro-2-mercaptobenzothiazole;4-Fluorobenzo[d]thiazole-2-thiol;4-Fluorobenzo[d]thiazole-2(3H)-thione
• CAS NO: 154327-24-9
• Molecular Formula: C₇H₄FNS₂
• Molecular Weight: 185.24
• Mol File: 154327-24-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 187-188℃
• Boiling Point: 286.1°C at 760 mmHg
• Flash Point: 126.8°C
• Appearance: /
• Density: 1.55
• Vapor Pressure: 0.00465mmHg at 25°C
• Refractive Index: 1.722
• CAS DataBase Reference: 4-Fluoro-2(3H)-Benzothiazolethione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-2(3H)-Benzothiazolethione(154327-24-9)
• EPA Substance Registry System: 4-Fluoro-2(3H)-Benzothiazolethione(154327-24-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 154327-24-9(Hazardous Substances Data)

Usage

General Description

4-Fluoro-2(3H)-benzothiazolethione is a chemical compound that belongs to the benzothiazolethione group. It is a thione derivative with a fluorine substitution at the 4-position of the benzothiazole ring. 4-Fluoro-2(3H)-benzothiazolethione has potential applications in pharmaceutical and agrochemical industries due to its biological activity and chemical properties. It is used in the synthesis of various heterocyclic compounds and may have potential as a drug candidate for the treatment of various diseases. Additionally, it may also be used as an intermediate in the chemical synthesis of other compounds with diverse applications.

InChI:InChI=1/C7H4FNS2/c8-4-2-1-3-5-6(4)9-7(10)11-5/h1-3H,(H,9,10)

Upstream product

• 363-51-9 2-chloro-6-fluoroaniline 
• 140-89-6 potassium ethyl xanthogenate 
• 75-15-0 carbon disulfide 
• 63755-09-9 6,6′-disulfanediylbis(2-fluoroaniline) 
• 5509-65-9 2,6-difluoroaniline 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 154327-25-0 4-fluoro-2-(methylthio)benzo[d]thiazole 
• 182344-56-5 2-chloro-4-fluoro benzothiazole 

Relevant articles and documents

Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof

The present invention provides compounds that can enhance functional O-mannosylation of proteins including alpha-dystroglycan. Also provided are methods of preparation of the compounds defined by the formula I. Also provided are the methods of using the compounds or the pharmaceutical acceptable salts or prodrugs thereof in treating and preventing subjects suffering from the diseases including muscular dystrophies and cancers.

Highly efficient synthesis of 2-mercaptobenzothiazole derivatives in water: Metal sulfide-disulfide dynamic interchange reaction

A convenient and efficient method for the synthesis of 2-mercaptobenzothiazoles from disulfide and CS2 mediated by a metal sulfide in water is described. This synthetic methodology could be used to prepare diverse 2-mercaptobenzothiazole derivatives in good to excellent yields. In this paper, the concept of metal sulfide-disulfide dynamic interchange reaction was put forward. Then the intermediates of the interchange reaction between NaHS and a disulfide were detected by LC-MS, which demonstrated that the S-S bond of the disulfide could be broken by the metal sulfide through the dynamic interchange reaction. In addition, NaHS was eventually transformed into sulfur S8 by the dynamic interchange reaction. Moreover, the underlying mechanism of 2-mercaptobenzothiazole formation is proposed, in which NaHS not only acts as an S-S bond cleaving agent but also as an activator of CS2. As a result, a novel synthetic route for the preparation of sulfur-containing heterocycles from a disulfide is developed.

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of α-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy.