Formula C7H5NS Density 1.24 g/cm³ | Molar mass 135.1863 g/mol | |
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Thermodynamicdata Phase behavioursolid–liquid–gas | ||
Benzothiazole is an aromatic heterocyclic compound with the chemical formula C
7H
5NS. It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature. A derivative of benzothiazole is the light-emitting component of luciferin, found in fireflies.
Contents
Structure and preparation
Benzothiazoles consist of a 5-membered 1,3-thiazole ring fused to a benzene ring. The nine atoms of the bicycle and the attached substituents are coplanar.
Benzothiazole are prepared by treatment of 2-mercaptoaniline with acid chlorides:
C6H4(NH2)SH + RC(O)Cl → C6H4(NH)SCR + HCl + H2OUses
This heterocyclic scaffold is readily substituted at the unique methyne centre in the thiazole ring. It is a thermally stable electron-withdrawing moiety with numerous applications in dyes such as thioflavin. Some drugs contain this group, examples being riluzole and pramipexole. The heterocycle is found in nature. Accelerators for the vulcanization of rubber are based on 2-mercaptobenzothiazole. This ring is a potential component in nonlinear optics (NLO). The compound is used also used as an insecticide and food flavoring agent.
