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
Preferred IUPAC name
1,3-Benzothiazole
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.002.179 Edit this at Wikidata
UNII
  • 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
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).
checkY verify (what is checkY☒N ?)

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.

Benzothiazoles are prepared by treatment of

acid chlorides:[1]

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

Uses

Benzothiazole occurs naturally in some foods but is also used as a food additive.[2] It has a sulfurous odor and meaty flavor.[3] The European Food Safety Authority assessment had "no safety concern at estimated levels of intake as a flavouring substance".[4]

The heterocyclic core of the molecule is readily substituted at the unique

2-mercaptobenzothiazoles.[6] This ring is a potential component in nonlinear optics (NLO).[7] A benzothiazole derivative is suggested as a dye for arsenic detection.[8]

See also

References

  1. ^ T. E. Gilchrist "Heterocyclic Chemistry" 3rd Edition, Longman, 1992.
  2. doi:10.1071/CH09126
  3. ^ "Benzothiazole". The Good Scents Company. Retrieved 2020-10-06.
  4. doi:10.2903/j.efsa.2008.875
    .
  5. S2CID 10421792
    .
  6. doi:10.1002/14356007.a23_365.pub2
  7. doi:10.1021/jp108623d
    .
  8. ISSN 1759-9679
    .

External links
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