Английская Википедия:Benzothiazole
Шаблон:Short description Шаблон:Chembox
Benzothiazole is an aromatic heterocyclic compound with the chemical formula Шаблон:Chem. 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.
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.
Benzothiazoles are prepared by treatment of 2-mercaptoaniline with acid chlorides:[1]
- 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.[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]
See also
- Benzothiazoles are related to thiazoles, which lack the fused benzene ring.
- Benzoxazoles, which substitute an oxygen for the sulfur atom.
References
External links
- ↑ T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
- ↑ Lucille Le Bozec, Christopher J. Moody "Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids" Australian Journal of Chemistry 62(7) 639–647.Шаблон:Doi
- ↑ Шаблон:Cite web
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
- ↑ Engels, H.-W., Weidenhaupt, H.-J., Pieroth, M., et al. "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. Шаблон:Doi
- ↑ Шаблон:Cite journal
- ↑ Шаблон:Cite journal
