Benzothiazole: Difference between revisions
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==Uses==
==Uses==
This heterocyclic scaffold 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]]. The heterocycle is found in nature.<ref>Lucille Le Bozec, Christopher J. Moody "Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids" Australian Journal of Chemistry 62(7) 639–647.{{doi|10.1071/CH09126}}</ref> Accelerators for the [[sulfur vulcanization]] of rubber are based on [[2-mercaptobenzothiazole]]s.<ref>Hans-Wilhelm Engels, Herrmann-Josef Weidenhaupt, Manfred Pieroth, Werner Hofmann, Karl-Hans Menting, Thomas Mergenhagen, Ralf Schmoll, Stefan Uhrlandt "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a23_365.pub2}}</ref> This ring is a potential component in [[nonlinear optics]] (NLO).<ref>{{Cite journal | journal = Journal of Physical Chemistry C | year = 2010 | volume = 114 | pages = 22289–22302 | last = Hrobarik | first = P. |author2=Sigmundova, I. |author3=Zahradnik, P. |author4=Kasak, P. |author5=Arion, V. |author6=Franz, E. |author7= Clays, K. | title = Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses? | doi = 10.1021/jp108623d | issue = 50}}</ref> The compound is also used as an [[insecticide]] and [[food flavoring]] agent. Benzothiazole, when combined with some chemicals{{Vague|reason=Unknown chemicals.|date=October 2020}},can be used as a dye in arsenic detection.''(see picture).''<ref>{{Cite journal|last=Chauhan|first=Kalpana|last2=Singh|first2=Prem|last3=Kumari|first3=Bhawana|last4=Singhal|first4=Rakesh Kumar|date=2017年03月16日|title=Synthesis of new benzothiazole Schiff base as selective and sensitive colorimetric sensor for arsenic on-site detection at ppb level|url=https://pubs.rsc.org/en/content/articlelanding/2017/ay/c6ay03302d|journal=Analytical Methods|language=en|volume=9|issue=11|pages=1779–1785|doi=10.1039/C6AY03302D|issn=1759-9679}}</ref>
This heterocyclic scaffold 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]]. The heterocycle is found in nature.<ref>Lucille Le Bozec, Christopher J. Moody "Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids" Australian Journal of Chemistry 62(7) 639–647.{{doi|10.1071/CH09126}}</ref> Accelerators for the [[sulfur vulcanization]] of rubber are based on [[2-mercaptobenzothiazole]]s.<ref>Hans-Wilhelm Engels, Herrmann-Josef Weidenhaupt, Manfred Pieroth, Werner Hofmann, Karl-Hans Menting, Thomas Mergenhagen, Ralf Schmoll, Stefan Uhrlandt "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a23_365.pub2}}</ref> This ring is a potential component in [[nonlinear optics]] (NLO).<ref>{{Cite journal | journal = Journal of Physical Chemistry C | year = 2010 | volume = 114 | pages = 22289–22302 | last = Hrobarik | first = P. |author2=Sigmundova, I. |author3=Zahradnik, P. |author4=Kasak, P. |author5=Arion, V. |author6=Franz, E. |author7= Clays, K. | title = Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses? | doi = 10.1021/jp108623d | issue = 50}}</ref> The compound is also used as an [[insecticide]] and [[food flavoring]] agent. Benzothiazole, when combined with some chemicals{{Vague|reason=Unknown chemicals.|date=October 2020}},can be used as a dye in arsenic detection.''(see picture).''<ref>{{Cite journal|last=Chauhan|first=Kalpana|last2=Singh|first2=Prem|last3=Kumari|first3=Bhawana|last4=Singhal|first4=Rakesh Kumar|date=2017年03月16日|title=Synthesis of new benzothiazole Schiff base as selective and sensitive colorimetric sensor for arsenic on-site detection at ppb level|url=https://pubs.rsc.org/en/content/articlelanding/2017/ay/c6ay03302d|journal=Analytical Methods|language=en|volume=9|issue=11|pages=1779–1785|doi=10.1039/C6AY03302D|issn=1759-9679}}</ref>
[[File:Benzothiazole reaction arsenic.gif|thumb]]
[[File:Benzothiazole_reaction_arsenic.gif|alt=|frameless|299x299px]]
Revision as of 13:59, 2 October 2020
Chemical compound
Benzothiazole
1,3-Benzothiazole
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
- n1c2ccccc2sc1
Except where otherwise noted, data are given for materials in their standard state (at 25°C [77°F], 100kPa).
Chemical compound
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.
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
This heterocyclic scaffold 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. The heterocycle is found in nature.[2] Accelerators for the sulfur vulcanization of rubber are based on 2-mercaptobenzothiazoles.[3] This ring is a potential component in nonlinear optics (NLO).[4] The compound is also used as an insecticide and food flavoring agent. Benzothiazole, when combined with some chemicals[vague ],can be used as a dye in arsenic detection.(see picture).[5]
File:Benzothiazole reaction arsenic.gif
See also
- Benzothiazoles are related to thiazoles, which lack the fused benzene ring.
- Benzoxazoles, which substitute an oxygen for the sulfur atom.
References
- ↑ 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.doi :10.1071/CH09126
- ↑ Hans-Wilhelm Engels, Herrmann-Josef Weidenhaupt, Manfred Pieroth, Werner Hofmann, Karl-Hans Menting, Thomas Mergenhagen, Ralf Schmoll, Stefan Uhrlandt "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH, Weinheim. doi :10.1002/14356007.a23_365.pub2
- ↑ Hrobarik, P.; Sigmundova, I.; Zahradnik, P.; Kasak, P.; Arion, V.; Franz, E.; Clays, K. (2010). "Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses?". Journal of Physical Chemistry C. 114 (50): 22289–22302. doi:10.1021/jp108623d.
- ↑ Chauhan, Kalpana; Singh, Prem; Kumari, Bhawana; Singhal, Rakesh Kumar (2017年03月16日). "Synthesis of new benzothiazole Schiff base as selective and sensitive colorimetric sensor for arsenic on-site detection at ppb level". Analytical Methods. 9 (11): 1779–1785. doi:10.1039/C6AY03302D. ISSN 1759-9679.