I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
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).
Hazard Statements: H302-H312-H331
Harmful if swallowed. Harmful in contact with skin. Toxic if inhaled.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P311-P312-P330-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Rinse mouth. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant