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Benzothiazole

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Benzothiazole
Space filling model of benzothiazole
Space filling model of benzothiazole
Ball-and-stick model of benzothiazole
Ball-and-stick model of benzothiazole
Names
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
Boiling point 227-228 °C
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 is an organosulfur compound. 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 luciferin, found in fireflies.

Structure and preparation

Benzothiazoles consist of a 5-membered 1,3-thiazole ring fused to a benzene ring. The eight atoms of the bicycle and the attached substituents are coplanar.

Benzothiazole are prepared by treatment of 2-aminobenzenethiol with acid chlorides:

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. Its a thermally stable electron-withdrawing moiety with numerous applications in dyes such as thioflavin. Some drugs contain this group, an example being riluzole. The heterocycle is found in nature. Accelerators for the vulcanization of rubber are based on 2-mercaptobenzothiazole. This ring is a potential component in nonlinear optics (NLO).

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. 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
  3. 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
  4. Hrobarik, P. (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: 22289–22302. doi:10.1021/10.1021/jp108623d. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

External links

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