Benzothiazole

Benzothiazole
Names
IUPAC name
1,3-Benzothiazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.179
UNII
Properties
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)
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

Benzothiazole 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 vulcanization of rubber are based on 2-mercaptobenzothiazole.[3] This ring is a potential component in nonlinear optics (NLO).[4] The compound is used also used as an insecticide and food flavoring agent.

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.; 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.
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