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Benzothiazole is an
aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
heterocyclic compound with the chemical formula . 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 Firefly luciferin (also known as beetle luciferin) is the luciferin, or light-emitting compound, used for the firefly (Lampyridae), railroad worm ( Phengodidae), starworm ( Rhagophthalmidae), and click-beetle (Pyrophorini) bioluminescent systems. ...
can be considered a derivative of benzothiazole.


Structure and preparation

Benzothiazoles consist of a 5-membered 1,3-
thiazole Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular fo ...
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 chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...
s: :C6H4(NH2)SH + RC(O)Cl → C6H4(NH)SCR + HCl + H2O


Uses

Benzothiazole occurs naturally in some foods but is also used as a food additive. It has a sulfurous odor and meaty flavor. The
European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, ...
assessment had "no safety concern at estimated levels of intake as a flavouring substance". 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. Some drugs contain this group, examples being riluzole and pramipexole. Accelerators for the sulfur vulcanization of rubber are based on 2-mercaptobenzothiazoles. This ring is a potential component in
nonlinear optics Nonlinear optics (NLO) is the branch of optics that describes the behaviour of light in ''nonlinear media'', that is, media in which the polarization density P responds non-linearly to the electric field E of the light. The non-linearity is typic ...
(NLO). A benzothiazole derivative is suggested as a dye for arsenic detection.


See also

* Benzothiazoles are related to
thiazole Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen. The term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular fo ...
s, which lack the fused benzene ring. * Benzoxazoles, which substitute an oxygen for the sulfur atom.


References


External links


MSDS
{{Simple aromatic rings Aromatic bases Simple aromatic rings