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Benzothiazole

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Title: Benzothiazole  
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Benzothiazole

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Benzothiazole

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Identifiers
CAS number 95-16-9 YesY
PubChem 7222
ChemSpider 6952 YesY
UNII G5BW2593EP YesY
ChEBI CHEBI:45993 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H5NS
Molar mass 135.19 g mol−1
Density 1.238 g/mL
Melting point

2 °C, 275 K, 36 °F

Boiling point

227-228 °C, 500-501 K, 441-442 °F

Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Benzothiazole is an aromatic heterocyclic compound with the chemical formula Template:Chem/link. 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 nine atoms of the bicycle and the attached substituents are coplanar.

Benzothiazole are prepared by treatment of 2-aminobenzenethiol 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. 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.[2] Accelerators for the vulcanization of rubber are based on 2-mercaptobenzothiazole.[3] This ring is a potential component in nonlinear optics (NLO).[4]

See also

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

References

External links

  • MSDS
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