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==Uses== ==Uses==
Benzothiazole occurs naturally in some foods but is also used as a ].<ref>{{cite journal | doi = Grandinin10.1071/CH09126 }}</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> 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>


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 }}</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> 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==

Latest revision as of 14:07, 3 September 2024

Chemical compound
Benzothiazole
Space filling model of benzothiazole
Space filling model of benzothiazole
Ball-and-stick model of benzothiazole
Ball-and-stick model of benzothiazole
Names
Preferred IUPAC name 1,3-Benzothiazole
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.179 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5HKey: IOJUPLGTWVMSFF-UHFFFAOYSA-N
  • InChI=1/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5HKey: IOJUPLGTWVMSFF-UHFFFAOYAC
SMILES
  • n1c2ccccc2sc1
Properties
Chemical formula C7H5NS
Molar mass 135.1863 g/mol
Density 1.238 g/mL
Melting point 2 °C (36 °F; 275 K)
Boiling point 227 to 228 °C (441 to 442 °F; 500 to 501 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Benzothiazole, or more specifically 1,3-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.

The three structural isomers of benzothizaole are 1,3-benzothiazole, 1,2-benzothiazole and 2,1-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:

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. It has a sulfurous odor and meaty flavor. The European Food Safety Authority assessment had "no safety concern at estimated levels of intake as a flavouring substance".

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. Some drugs contain this group, examples being riluzole and pramipexole. Accelerators for the sulfur vulcanization of rubber are based on 2-mercaptobenzothiazoles. This ring is a potential component in nonlinear optics (NLO). A benzothiazole derivative is suggested as a dye for arsenic detection.

See also

  • Benzothiazoles are related to thiazoles, which lack the fused benzene ring.
  • Benzoxazoles, which substitute an oxygen for the sulfur atom.

References

  1. T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
  2. Le Bozec, Lucille; Moody, Christopher J. (2009). "Naturally Occurring Nitrogen–Sulfur Compounds. The Benzothiazole Alkaloids". Australian Journal of Chemistry. 62 (7): 639. doi:10.1071/CH09126.
  3. "Benzothiazole". The Good Scents Company. Retrieved 2020-10-06.
  4. "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". EFSA Journal. 6 (11): 875. 2008. doi:10.2903/j.efsa.2008.875.
  5. Gill, Rupinder K.; Rawal, Ravindra K.; Bariwal, Jitender (2015). "Recent Advances in the Chemistry and Biology of Benzothiazoles". Archiv der Pharmazie. 348 (3): 155–178. doi:10.1002/ardp.201400340. PMID 25682746. S2CID 10421792.
  6. Engels, Hans-Wilhelm; Weidenhaupt, Herrmann-Josef; Pieroth, Manfred; Hofmann, Werner; Menting, Karl-Hans; Mergenhagen, Thomas; Schmoll, Ralf; Uhrlandt, Stefan (2004), "Rubber, 4. Chemicals and Additives", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a23_365.pub2, ISBN 3-527-30673-0
  7. Hrobarik, P.; Sigmundova, I.; Zahradnik, P.; et al. (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.
  8. Chauhan, Kalpana; Singh, Prem; Kumari, Bhawana; Singhal, Rakesh Kumar (2017-03-16). "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.

External links

Simple aromatic rings
1 ring
Three-membered
Five-membered
Six-membered
Seven-membered
Nine-membered
18-membered
2 rings
Five + Five
Five + Six
Six + Six
Five + Seven
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