Benzothiazole

Names

IUPAC name

1,3-Benzothiazole

Identifiers

CAS Number

95-16-9^Y

3D model (Jmol)

CHEBI:45993^Y

ChEMBL510309^Y

6952^Y

G5BW2593EP^Y

InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H^Y

Key: IOJUPLGTWVMSFF-UHFFFAOYSA-N^Y
InChI=1/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H

Key: IOJUPLGTWVMSFF-UHFFFAOYAC

SMILES

n1c2ccccc2sc1

Properties

C₇H₅NS

135.1863 g/mol

1.238 g/mL

2 °C (36 °F; 275 K)

227 to 228 °C (441 to 442 °F; 500 to 501 K)

Supplementary data page

Structure and
properties

Refractive index (n),
Dielectric constant (ε_r), etc.

Thermodynamic
data

Phase behaviour
solid–liquid–gas

Spectral data

UV, IR, NMR, MS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

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. A derivative of benzothiazole is the light-emitting component of luciferin, found in fireflies.

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:

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

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