51618-30-5

Basic information

• Product Name: 6-Bromo-2-mercaptobenzothiazole
• Synonyms: 6-Bromo-2-mercaptobenzothiazole;2-Mercapto-6-bromobenzothiazole;6-Bromo-2(3H)-benzothiazolethione;6-Bromobenzo[d]thiazole-2-thiol;6-broMo-1,3-benzothiazole-2-thiol;6-BroMobenzo[d]thiazole-2(3H)-thione
• CAS NO: 51618-30-5
• Molecular Formula: C₇H₄BrNS₂
• Molecular Weight: 246.15
• Product Categories: Heterocycles;Heterocyclic Compound;API intermediates
• Mol File: 51618-30-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 260-263 °C
• Boiling Point: 359.7 °C at 760 mmHg
• Flash Point: 171.3 °C
• Appearance: powder
• Density: 1.93
• Vapor Pressure: 2.34E-05mmHg at 25°C
• Refractive Index: 1.827
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.15±0.20(Predicted)
• CAS DataBase Reference: 6-Bromo-2-mercaptobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-mercaptobenzothiazole(51618-30-5)
• EPA Substance Registry System: 6-Bromo-2-mercaptobenzothiazole(51618-30-5)

Safety Data

• Hazardous Substances Data: 51618-30-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

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

Upstream product

• 80945-86-4 6-bromo-2-chloro-benzothiazole 
• 66416-72-6 4-bromo-2-iodoaniline 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 53218-26-1 6-bromo-1,3-benzothiazole 
• 182499-80-5 2,2′-disulfanediylbis(4-bromoaniline) 
• 75-15-0 carbon disulfide 
• 615-57-6 2,4-dibromo-aniline 
• 140-89-6 potassium ethyl xanthogenate 
• 367-24-8 4-bromo-2-fluoroaniline 
• 28563-38-4 ethylxanthogenate 

Downstream Products

• 474966-97-7 6-bromo-2-(methylsulfanyl)benzothiazole 

Relevant articles and documents

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.

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.

An efficient copper-catalyzed synthesis of 2-mercaptobenzothiazole through S-arylation/heterocyclization of 2-haloaniline with potassium xanthate

A mild and efficient methodology to produce 2-mercaptobenzothiazoles in DMF via ortho-haloaniline coupling with potassium O-ethyl dithiocarbonate catalyzed by copper without a ligand has been developed.