315228-79-6

Basic information

• Product Name: 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI)
• Synonyms: 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI);2,3-Dihydro-2-thioxo-6-benzothiazolecarbonitrile;2-Mercapto-1,3-benzothiazole-6-carbonitrile;2-Mercaptobenzothiazole-6-carbonitrile;6-Benzothiazolecarbonitrile, 2,3-dihydro-2-thioxo-;2-Mercaptobenzo[d]thiazole-6-carbonitrile
• CAS NO: 315228-79-6
• Molecular Formula: C₈H₄N₂S₂
• Molecular Weight: 192.26076
• Product Categories: BENZOTHIAZOLE
• Mol File: 315228-79-6.mol

Chemical Properties

• Boiling Point: 369.38 °C at 760 mmHg
• Flash Point: 177.195 °C
• Appearance: /
• Density: 1.54
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI)(315228-79-6)
• EPA Substance Registry System: 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI)(315228-79-6)

Safety Data

• Hazardous Substances Data: 315228-79-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) is utilized as a key intermediate in the synthesis of pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Production:
In the agrochemical industry, 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) is employed as a building block for the creation of new agrochemicals. Its incorporation can lead to the development of more effective and targeted pesticides or herbicides.
Used in Dye Manufacturing:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) is used as a component in the production of dyes. Its chemical properties contribute to the color and stability of the resulting dyes, making it a valuable asset in the dye industry.
Used in Organic Electronic Materials:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) has been investigated for its potential use in organic electronic materials. Its electronic properties make it a candidate for applications in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and other electronic devices.
Used in Photovoltaic Devices:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) has also been studied for its potential application in photovoltaic devices. Its ability to absorb and transport charge carriers makes it a promising material for improving the efficiency and performance of solar cells.
Used in Antimicrobial Applications:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) has demonstrated antimicrobial properties, making it a potential candidate for use in the development of new antimicrobial agents to combat resistant bacteria and other pathogens.
Used in Antifungal Applications:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) has also shown antifungal activity, indicating its potential use in the development of antifungal drugs to treat fungal infections.
Used in Antitumor Research:
6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI) has been studied for its antitumor properties, suggesting its potential as a chemotherapeutic agent or a component in the development of targeted cancer therapies.
Safety Information:
Before handling or using 6-Benzothiazolecarbonitrile,2,3-dihydro-2-thioxo-(9CI), it is crucial to consult safety information to ensure proper handling, storage, and disposal to minimize potential health and environmental risks.

Upstream product

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Downstream Products

• 315228-91-2 2-(2-chloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrile 
• 80945-83-1 2-chloro-1,3-benzothiazole-6-carbonitrile 
• 315228-90-1 2-(2,6-dichloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrile 

Relevant articles and documents

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles

Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.

Metal sulfide: An efficient promoter for the synthesis of 2-mercaptobenzothiazoles from 2-haloanilines and carbon disulfide

A convenient method has been developed for the preparation of a variety of 2-mercaptobenzothiazoles from 2-haloanilines and CS2 mediated by metal sulfide. In this reaction, 2-haloanilines reacted with CS2 in the presence of Na2S · 9H2O to form 2-mercaptobenzothiazoles. Na2S · 9H2O functioned both as an activator of CS2 and as a base. Furthermore, NMR analysis was used to identify the different reaction mechanisms of 2-haloanilines and CS2 mediated by Na2S or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which demonstrated that Na2S interacted only with CS2, while DBU reacted with both 2-iodoaniline and CS2.

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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.

Efficient, Iron-Catalyzed Synthesis of 2-Mercaptobenzothiazole Through S-Arylation/Heterocyclization of 2-Haloaniline with Potassium Xanthate

A mild and practical method for the synthesis of 2-mercaptobenzothiazole has been developed by using iron as an efficient catalyst. The present tandem reaction process allows access to a wide range of 2-mercaptobenzothiazoles in good to excellent yields by the reaction of 2-haloaniline with potassium O-ethyl dithiocarbonate in the presence of FeF3 as a catalyst and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand under an atmosphere of argon.

Synthesis of 2-mercaptobenzothiazoles via DBU-promoted tandem reaction of o-haloanilines and carbon disulfide

An efficient strategy for the synthesis of a variety of 2-mercaptobenzothiazole derivatives has been developed. The reaction proceeded from o-haloaniline derivatives and carbon disulfide via a tandem reaction in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford the corresponding 2-mercaptobenzothiazole derivatives in good to excellent yields.

Therapeutic modulation of PPARgamma activity

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Compounds for the modulation of PPARgamma activity

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