Benzothiazole
Encyclopedia
Benzothiazole is an aromatic heterocyclic compound
with the chemical formula . 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.
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:
. 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).
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
with the chemical formula . 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
Luciferin
Luciferins are a class of light-emitting biological pigments found in organisms that cause bioluminescence...
, found in fireflies.
Structure and preparation
Benzothiazoles consist of a 5-membered 1,3-thiazoleThiazole
Thiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen; the term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS...
ring fused
Annulation
Annulation in organic chemistry is a chemical reaction in which a new ring is constructed on another molecule ....
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 thioflavinThioflavin
Thioflavin can refer to either of two dyes used for histology staining and biophysical studies of protein aggregation.Thioflavin T is a benzothiazole salt obtained by the methylation of dehydrothiotoluidine with methanol in the presence of hydrochloric acid...
. Some drugs contain this group, an example being riluzole
Riluzole
Riluzole is a drug used to treat amyotrophic lateral sclerosis. It delays the onset of ventilator-dependence or tracheostomy in selected patients and may increase survival by approximately 3–5 months....
. The heterocycle is found in nature. Accelerators for the vulcanization
Vulcanization
Vulcanization or vulcanisation is a chemical process for converting rubber or related polymers into more durable materials via the addition of sulfur or other equivalent "curatives." These additives modify the polymer by forming crosslinks between individual polymer chains. Vulcanized material is...
of rubber are based on 2-mercaptobenzothiazole. This ring is a potential component in nonlinear optics
Nonlinear optics
Nonlinear optics is the branch of optics that describes the behavior of light in nonlinear media, that is, media in which the dielectric polarization P responds nonlinearly to the electric field E of the light...
(NLO).
See also
- Benzothiazoles are related to thiazoleThiazoleThiazole, or 1,3-thiazole, is a heterocyclic compound that contains both sulfur and nitrogen; the term 'thiazole' also refers to a large family of derivatives. Thiazole itself is a pale yellow liquid with a pyridine-like odor and the molecular formula C3H3NS...
s, which lack the fused benzene ring. - BenzoxazoleBenzoxazoleBenzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine. Benzoxazole is used primarily in industry and research, and has no household use....
s, which substitute an oxygen for the sulfur atom.