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. Firefly luciferin can be considered a derivative of benzothiazole.
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Names | |||
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Preferred IUPAC name
1,3-Benzothiazole | |||
Identifiers | |||
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3D model (JSmol)
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ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.002.179 | ||
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |||
C7H5NS | |||
Molar mass | 135.1863 g/mol | ||
Density | 1.238 g/mL | ||
Melting point | 2 °C (36 °F; 275 K) | ||
Boiling point | 227 to 228 °C (441 to 442 °F; 500 to 501 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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.
Benzothiazoles are prepared by treatment of 2-mercaptoaniline with acid chlorides:[1]
Benzothiazole occurs naturally in some foods but is also used as a food additive.[2] It has a sulfurous odor and meaty flavor.[3] The European Food Safety Authority assessment had "no safety concern at estimated levels of intake as a flavouring substance".[4]
The heterocyclic core of the molecule 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.[5] Some drugs contain this group, examples being riluzole and pramipexole. Accelerators for the sulfur vulcanization of rubber are based on 2-mercaptobenzothiazoles.[6] This ring is a potential component in nonlinear optics (NLO).[7] A benzothiazole derivative is suggested as a dye for arsenic detection.[8]