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It is an interesting carbonyl equivalent and reacts with aldehydes or ketones to generate α-hydroxy carbonyl compounds. Benzothiazole is used as a chemical intermediate in organic synthesis. It is a precursor of rubber accelerators and a component of cyanine dyes. It is also used as a flavoring substance. It is also used as a flavor, antimicrobial agent, and component of cyanine dyes. Its derivatives are used as rubber accelerators.
Nawrocki ST, et al. Comparative aquatic toxicity evaluation of 2-(thiocyanomethylthio)benzothiazole and selected degradation products using Ceriodaphnia dubia. Arch. Environ. Contam. Toxicol.,2005,48(3), 344-350.
Asimakopoulos AG, et al. Occurrence and removal efficiencies of benzotriazoles and benzothiazoles in a wastewater treatment plant in Greece. The Science of the total environment.,2013,452-453163-171.
n-BuLi gives the 2-lithio-derivative, stable below -50o, which behaves as a formyl anion equivalent, reacting with aldehydes and ketones. The derived alcohols have been transformed into various useful products, e.g. ɑ-hydroxy ketones: Tetrahedron Lett., 5, 9, 13, (1978); Bull. Chem. Soc. Jpn., 61, 3637 (1988):
The lithio-derivative can also be acylated with esters, lactones, amides or nitriles. In these applications, benzothiazole is claimed to be superior to the better known 1,3-dithiane as a formyl anion synthon.
Reaction of the lithio-derivative at low temperatures with PCl3 gives, as the major product, 2,2'-bibenzothiazole instead of the expected tertiary phosphine: Heterocycles, 30, 347 (1990). POCl3 or SOCl2 also promote the symmetrical coupling reaction: Heteroatom. Chem., 5, 409 (1994).
Gefahrenhinweise (EU): H301-H311-H332-H319
Toxic if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes serious eye irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER/doctor IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.