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{{short description|Chemical compound}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 405015451 | verifiedrevid = 443417223
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Benzothiazole numbering.png | ImageFile = Benzothiazole numbering.png
| ImageSize = 150px | ImageSize = 150px
| ImageFileL1 = Benzothiazole-space-filling.png | ImageFileL1 = Benzothiazole-space-filling.png
⚫ | ImageNameL1 = Space filling model of benzothiazole
| ImageSizeL1 = 100px
| ImageFileR1 = Benzothiazole-ball-and-stick.png
⚫ | ImageNameL1 = Space filling model of benzothiazole
| ImageFileR1 = Benzothiazole-ball-and-stick.png | ImageNameR1 = Ball-and-stick model of benzothiazole
⚫ | PIN = 1,3-Benzothiazole
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of benzothiazole
⚫ | IUPACName = 1,3-Benzothiazole
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6952 | ChemSpiderID = 6952
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| StdInChIKey = IOJUPLGTWVMSFF-UHFFFAOYSA-N | StdInChIKey = IOJUPLGTWVMSFF-UHFFFAOYSA-N
| CASNo = 95-16-9 | CASNo = 95-16-9
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 7222 | PubChem = 7222
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G5BW2593EP | UNII = G5BW2593EP
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 45993 | ChEBI = 45993
| SMILES = n1c2ccccc2sc1 | SMILES = n1c2ccccc2sc1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = | Formula =
| C=7 | H=5 | N=1 | S=1 | C=7 | H=5 | N=1 | S=1
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| Appearance = | Appearance =
| Density = 1.238 g/mL | Density = 1.238 g/mL
| MeltingPt = 2 °C | MeltingPtC = 2
| BoilingPt = 227-228 °C | BoilingPtC = 227 to 228
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}
'''Benzothiazole''' is an ]. 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. A derivative of benzothiazole is the light-emitting component of ], found in fireflies. '''Benzothiazole''', or more specifically '''1,3-benzothiazole''', is an ] ] with the chemical formula {{Chem|C|7|H|5|N||S}}. 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. ] can be considered a derivative of benzothiazole.

The three ] of benzothizaole are 1,3-benzothiazole, 1,2-benzothiazole and 2,1-benzothiazole.


==Structure and preparation== ==Structure and preparation==
Benzothiazoles consist of a 5-membered 1,3-] ring ] to a benzene ring. The eight atoms of the bicycle and the attached substituents are coplanar. Benzothiazoles consist of a 5-membered 1,3-] ring ] to a benzene ring. The nine atoms of the bicycle and the attached substituents are coplanar.


Benzothiazole are prepared by treatment of 2-aminobenzenethiol with ]s:<ref>T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.</ref> Benzothiazoles are prepared by treatment of ] with ]s:<ref>T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.</ref>
:C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)SH + RC(O)Cl → C<sub>6</sub>H<sub>4</sub>(NH)SCR + HCl + H<sub>2</sub>O :C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)SH + RC(O)Cl → C<sub>6</sub>H<sub>4</sub>(NH)SCR + HCl + H<sub>2</sub>O


==Uses== ==Uses==
Benzothiazole occurs naturally in some foods but is also used as a ].<ref>{{cite journal | doi = 10.1071/CH09126 | title = Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids | date = 2009 | last1 = Le Bozec | first1 = Lucille | last2 = Moody | first2 = Christopher J. | journal = Australian Journal of Chemistry | volume = 62 | issue = 7 | page = 639 }}</ref> It has a sulfurous ] and meaty flavor.<ref>{{cite web |url=http://www.thegoodscentscompany.com/data/rw1007521.html |title=Benzothiazole |website=The Good Scents Company |access-date=2020-10-06 }}</ref> The ] assessment had "no safety concern at estimated levels of intake as a flavouring substance".<ref>{{cite journal |doi=10.2903/j.efsa.2008.875 |doi-access=free|title=Flavouring Group Evaluation 76, (FGE.76) - Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29, miscellaneous |journal=EFSA Journal |year=2008 |volume=6 |issue=11 |page=875 }}</ref>
This heterocyclic scaffold is readily substituted at the unique methyne centre in the thiazole ring. Its a thermally stable electron-withdrawing moiety with numerous applications in dyes such as ]. Some drugs contain this group, an example being ]. 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 ] of rubber are based on 2-mercaptobenzothiazole.<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 ] (NLO).<ref>{{Cite journal | journal = Journal of Physical Chemistry C | year = 2010 | volume = 114 | pages = 22289–22302 | last = Hrobarik | first = P. | coauthors = Sigmundova, I.; Zahradnik, P.; Kasak, P.; Arion, V.; Franz, E.; Clays, K. | title = Molecular Engineering of Benzothiazolium Salts with Large Quadratic Hyperpolarizabilities: Can Auxiliary Electron-Withdrawing Groups Enhance Nonlinear Optical Responses? | doi = 10.1021/10.1021/jp108623d}}</ref>

The heterocyclic core of the molecule is readily substituted at the unique ] centre in the thiazole ring. It is a thermally stable electron-withdrawing moiety with numerous applications in dyes such as ].<ref>{{cite journal |doi=10.1002/ardp.201400340|title=Recent Advances in the Chemistry and Biology of Benzothiazoles |year=2015 |last1=Gill |first1=Rupinder K. |last2=Rawal |first2=Ravindra K. |last3=Bariwal |first3=Jitender |journal=Archiv der Pharmazie |volume=348 |issue=3 |pages=155–178 |pmid=25682746 |s2cid=10421792 |doi-access=free }}</ref> Some drugs contain this group, examples being ] and ]. Accelerators for the ] of rubber are based on ]s.<ref>{{citation | doi = 10.1002/14356007.a23_365.pub2 | chapter = Rubber, 4. Chemicals and Additives | title = Ullmann's Encyclopedia of Industrial Chemistry | date = 2004 | last1 = Engels | first1 = Hans-Wilhelm | last2 = Weidenhaupt | first2 = Herrmann-Josef | last3 = Pieroth | first3 = Manfred | last4 = Hofmann | first4 = Werner | last5 = Menting | first5 = Karl-Hans | last6 = Mergenhagen | first6 = Thomas | last7 = Schmoll | first7 = Ralf | last8 = Uhrlandt | first8 = Stefan | isbn = 3-527-30673-0 }}</ref> This ring is a potential component in ] (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. |display-authors=3| 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> A benzothiazole derivative is suggested as a dye for arsenic detection.<ref>{{Cite journal|last1=Chauhan|first1=Kalpana|last2=Singh|first2=Prem|last3=Kumari|first3=Bhawana|last4=Singhal|first4=Rakesh Kumar|date=2017-03-16|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>


==See also== ==See also==
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==References== ==References==
{{Reflist}}
<references/>

==External links== ==External links==
* *

{{Simple aromatic rings}}


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