Benzothiazole

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Benzothiazole
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Names
Preferred IUPAC name
1,3-Benzothiazole
Identifiers
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3D model (JSmol)
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  • InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H checkY
    Key: IOJUPLGTWVMSFF-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
    Key: IOJUPLGTWVMSFF-UHFFFAOYAC
  • n1c2ccccc2sc1
Properties
C7H5NS
Molar mass 135.1863 g/mol
Appearance colorless liquid
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 [77 °F], 100 kPa).

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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.[1] It has a sulfurous odor and meaty flavor.[2]

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

Structure and reactivity

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. The heterocyclic core of the molecule is readily substituted at the methyne (CH) centre in the thiazole ring. Thiazole is electron-withdrawing.

Synthesis and biosynthesis

Benzothiazoles are typically prepared by treatment of 2-mercaptoaniline.[3] For example, acid chlorides are effective:[4]

C6H4(NH2)SH + RC(O)Cl → C6H4(N)SCR + HCl + H2O

Many other precursors have been used, commonly aldehydes in the presence of oxidants. In some cases, benzothiazoles are prepared directly from anilines, a process that entails ortho functionalization.[5]

Naturally occurring benzothiazoles are proposed to arise by condensation of cysteine with quinones.[1]

Uses

Dyes

The dye thioflavin is a benzothiazole derivative.[6]

Food additives

Benzothiazole occurs naturally in some foods but is also used as a food additive.[1] It has a sulfurous odor and meaty flavor.[7] The European Food Safety Authority assessment had "no safety concern at estimated levels of intake as a flavouring substance".[8]

Rubber additive

Accelerators for the sulfur vulcanization of rubber are based on 2-mercaptobenzothiazoles.[9]

Pharmacology

File:Ziprasidone.svg
Ziprasidone is used to treat schizophrenia and bipolar disorder.

Benzothiazoles have been widely investigated for their bioactivity.[10][11] The benzothiazole moiety is, for example, seen in certain dopamine-acting drugs, e.g. riluzole and pramipexole. Moreover, benzothiazole derivatives act as monoamine oxidase inhibitors or dopamine antagonists:

See also

Safety and environmental considerations

Benzothiazoles are widely used in the vulcanization of rubber, so their possible role in the environment has attracted attention. Evidence suggests that they biodegrade readily.[17]

References

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  1. ^ a b c Page Module:Citation/CS1/styles.css has no content.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.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Benzothiazole". The Good Scents Company. Retrieved 2020-10-06.
  3. ^ Page Module:Citation/CS1/styles.css has no content.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.
  4. ^ T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Würfel, Hendryk; Jakobi, Dörthe (2018). "Syntheses of Substituted 2-Cyano-benzothiazoles". Organic Syntheses. 95: 177–191. doi:10.15227/orgsyn.095.0177.
  6. ^ Page Module:Citation/CS1/styles.css has no content.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.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Benzothiazole". The Good Scents Company. Retrieved 2020-10-06.
  8. ^ Page Module:Citation/CS1/styles.css has no content."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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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
  10. ^ Page Module:Citation/CS1/styles.css has no content.Rouf, Abdul; Tanyeli, Cihangir (2015). "Bioactive thiazole and benzothiazole derivatives". European Journal of Medicinal Chemistry. 97: 911–927. doi:10.1016/j.ejmech.2014.10.058. hdl:11511/43872. PMID 25455640.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Keri, Rangappa S.; Patil, Mahadeo R.; Patil, Siddappa A.; Budagumpi, Srinivasa (2015). "A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry". European Journal of Medicinal Chemistry. 89: 207–251. doi:10.1016/j.ejmech.2014.10.059. PMID 25462241.
  12. ^ Page Module:Citation/CS1/styles.css has no content.le Roux, Anandie; Petzer, Anél; Cloete, Stephanus J.; Petzer, Jacobus P. (2025-03-01). "An investigation of the monoamine oxidase inhibition properties of benzothiazole derivatives". Results in Chemistry. 14 102142. doi:10.1016/j.rechem.2025.102142. ISSN 2211-7156.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Acar Çevik, Ulviye; Osmaniye, Derya; Sağlik, Begüm N.; Levent, Serkan; K. Çavuşoğlu, Betül; Karaduman, Abdullah B.; D. Özkay, Ümide; Özkay, Yusuf; Kaplancikli, Zafer A.; Turan, Gülhan (2020). "Synthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors". Journal of Heterocyclic Chemistry. 57 (5): 2225–2233. doi:10.1002/jhet.3942. ISSN 1943-5193.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Turan, Gülhan; Osmaniye, Derya; Sağlik, Begüm Nurpelin; Çevik, Ulviye Acar; Levent, Serkan; Çavuşoğlu, Betül Kaya; Özkay, Ümide Demir; Özkay, Yusuf; Kaplancikli, Zafer Asım (2020-06-02). "Synthesis and monoamine oxidase A/B inhibitory evaluation of new benzothiazole-thiazolylhydrazine derivatives". Phosphorus, Sulfur, and Silicon and the Related Elements. 195 (6): 491–497. doi:10.1080/10426507.2020.1722667. ISSN 1042-6507.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Boateng, Comfort A.; Nilson, Ashley N.; Placide, Rebekah; Pham, Mimi L.; Jakobs, Franziska M.; Boldizsar, Noelia; McIntosh, Scot; Stallings, Leia S.; Korankyi, Ivana V.; Kelshikar, Shreya; Shah, Nisha; Panasis, Diandra; Muccilli, Abigail; Ladik, Maria; Maslonka, Brianna (2023-09-14). "Pharmacology and Therapeutic Potential of Benzothiazole Analogues for Cocaine Use Disorder". Journal of Medicinal Chemistry. 66 (17): 12141–12162. doi:10.1021/acs.jmedchem.3c00734. ISSN 0022-2623. PMC 10510399. PMID 37646374.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Sampson, Dinithia; Zhu, Xue Y.; Eyunni, Suresh V. K.; Etukala, Jagan R.; Ofori, Edward; Bricker, Barbara; Lamango, Nazarius S.; Setola, Vincent; Roth, Bryan L.; Ablordeppey, Seth Y. (2014-06-15). "Identification of a new selective dopamine D4 receptor ligand". Bioorganic & Medicinal Chemistry. 22 (12): 3105–3114. doi:10.1016/j.bmc.2014.04.026. ISSN 0968-0896. PMC 4096627. PMID 24800940.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Clarke, Bradley O.; Smith, Stephen R. (2011). "Review of 'emerging' organic contaminants in biosolids and assessment of international research priorities for the agricultural use of biosolids". Environment International. 37 (1): 226–247. Bibcode:2011EnInt..37..226C. doi:10.1016/j.envint.2010.06.004. PMID 20797791.

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