2602-85-9

Basic information

• Product Name: 2-Benzothiazolecarbonitrile(7CI,8CI,9CI)
• Synonyms: 2-Benzothiazolecarbonitrile(7CI,8CI,9CI);Benzo[d]thiazole-2-carbonitrile;2-benzothiazolecarbonitrile;2-CYANO-BENZO[D]THIAZOLE
• CAS NO: 2602-85-9
• Molecular Formula: C₈H₄N₂S
• Molecular Weight: 160.2
• Product Categories: BENZOTHIAZOLE
• Mol File: 2602-85-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 80 °C
• Boiling Point: 293.2±23.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -2.24±0.10(Predicted)
• CAS DataBase Reference: 2-Benzothiazolecarbonitrile(7CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzothiazolecarbonitrile(7CI,8CI,9CI)(2602-85-9)
• EPA Substance Registry System: 2-Benzothiazolecarbonitrile(7CI,8CI,9CI)(2602-85-9)

Safety Data

• Hazardous Substances Data: 2602-85-9(Hazardous Substances Data)

Usage

General Description

2-Benzothiazolecarbonitrile is a chemical compound with the formula C9H5NS. It is a benzothiazole derivative, which is a common structural motif in many pharmaceutical and agrochemical compounds. 2-Benzothiazolecarbonitrile(7CI,8CI,9CI) is used as an intermediate in the synthesis of various heterocyclic compounds and dyes. It is also used in the manufacture of rubber antioxidants and fungicides. Additionally, 2-Benzothiazolecarbonitrile has potential biological activity and is being studied for its potential use in the development of pharmaceutical compounds.

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 67219-33-4 2-phenylmethanesulfonyl-benzothiazole 
• 2408-36-8 lithium cyanide 
• 136-95-8 2-amino-benzthiazole 
• 67-66-3 chloroform 
• 29389-34-2 benzothiazol-2-yl-(E)-hydroxyimino-acetic acid 

Downstream Products

• 57870-97-0 Benzothiazol-2-carbimidsaeure-methylester 
• 29737-44-8 N-(benzothiazole-2-carboximidoyl)-DL-phenylalanine ethyl ester 
• 29782-01-2 N-(benzothiazole-2-carboximidoyl)-L-phenylalanine tert-butyl ester 
• 64377-94-2 benzo[d]thiazole-2-carbothioamide 
• 188672-83-5 6-nitro-1,3-benzothiazole-2-carbonitrile 
• 7724-12-1 2-cyano-6-aminobenzothiazole 
• 1259033-29-8 (-)-(1'R,3R)-5-(benzothiazol-2-yl)-3-phenyl-2-(1-phenylethyl)-2,3-dihydro-1,2,4-oxadiazole 
• 1259033-30-1 (+)-(1'R,3S)-5-(benzothiazol-2-yl)-3-phenyl-2-(1-phenylethyl)-2,3-dihydro-1,2,4-oxadiazole 
• 29781-96-2 N-(benzothiazole-2-carboximidoyl)-DL-phenylalanine 
• 29804-86-2 2-benzothiazol-2-yl-5-benzyl-3,5-dihydro-imidazol-4-one 

Relevant articles and documents

Eco-Friendly Microwave-Assisted Scaleable Synthesis of 2-Cyanobenzothiazoles via N-Arylimino-1,2,3-dithiazoles

The cyclization procedure of N-aryl iminodithiazoles into 2-cyanobenzothiazoles was re-investigated with the aim to develop original and environmentally friendly procedures. In this article, the benefits associated with the microwave methodology are reported and the opportunity to use solvent-free procedures in order to scale up organic synthesis is studied. The result obtained show that the strong thermal effects due to graphite/microwaves interaction can be efficiently used for the synthesis of heterocyclic molecules for which traditional methods failed or are less attractive.

Stereochemistry of the olefin formation from anti and syn heterocyclic β-hydroxy sulfones.

Reaction of aldehydes R2-CHO with the new lithio derivatives of 2-benzothiazoles or pyridines R1-CH2-SO2-Het afforded the corresponding β-hydroxy sulfones which are stable in the pyridine series and generally unstable in the benzothiazole series except for anti derivatives 10a and 20c. t-Butyl-dimethyl silyl ethers of all the heterocyclic β-hydroxy sulfones have been obtained by oxidation of the corresponding anti and syn sulfides, which have been stereoselectively prepared from the epoxides 17, 19, 21 and 23.The lithium or tetrabutylammonium alkoxides of heterocyclic β-hydroxy sulfones undergo an intramolecular addition to the neighboring C=N group followed by an S to O benzothiazole (or pyridine) transfer, and simultaneous extrusion of sulfur dioxide, ejection of benzothiazol-2(3H)-one anion and formation of the corresponding olefins.From the data of twenty cases studied, it can be concluded that the final elimination is entirely antiperiplanar only for the alkoxides of β-hydroxy-BT- or Pyr-sulfones anti or syn bearing saturated aliphatic chains R1 and R2 and for anti derivatives with R1 = R2 = C6H5.Due to their equilibration however, the alkoxides of numerous derivatives of heterocyclic (3-methylbut-2-enyl) or (phenylmethyl) sulfones do not follow entirely the above antiperiplanar elimination. Keywords: heteroaromatic sulfones / intramolecular ipso reaction / organolithium derivatives / stereochemistry / eliminations / olefination