Thiazole

Names

Preferred IUPAC name

1,3-Thiazole

Other names

Thiazole

Identifiers

CAS Number

288-47-1^Y

3D model (Jmol)

CHEBI:43732^Y

ChEMBL15605^Y

8899^Y

320RCW8PEF^Y

InChI=1S/C3H3NS/c1-2-5-3-4-1/h1-3H^Y

Key: FZWLAAWBMGSTSO-UHFFFAOYSA-N^Y
InChI=1/C3H3NS/c1-2-5-3-4-1/h1-3H

Key: FZWLAAWBMGSTSO-UHFFFAOYAI

SMILES

n1ccsc1

Properties

Chemical formula

C₃H₃NS

Molar mass

85.12 g·mol⁻¹

Boiling point

116 to 118 °C (241 to 244 °F; 389 to 391 K)

Acidity (pK_a)

2.5 (of conjugate acid)

Magnetic susceptibility (χ)

-50.55·10⁻⁶ cm³/mol

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

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. The thiazole ring is notable as a component of the vitamin thiamine (B₁).

Thiazoles are members of the azoles, heterocycles that include imidazoles and oxazoles. Thiazole can also be considered a functional group. Oxazoles are related compounds, with sulfur replaced by oxygen. Thiazoles are structurally similar to imidazoles, with the thiazole sulfur replaced by nitrogen.

Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. This aromaticity is evidenced by the chemical shift of the ring protons in proton NMR spectroscopy (between 7.27 and 8.77 ppm), clearly indicating a strong diamagnetic ring current. The calculated pi-electron density marks C5 as the primary site for electrophilic substitution, and C2 as the site for nucleophilic substitution.

Thiazoles are found in a variety of specialized products, often fused with benzene derivatives, the so-called benzothiazoles. In addition to vitamin B₁, the thiazole ring is found in epothilone. Other important thiazole dervatives are benzothiazoles, for example, the firefly chemical luciferin. Whereas thiazoles are well represented in biomolecules, oxazoles are not.

Commercial significant thiazoles include mainly dyes and fungicides. Thifluzamide, Tricyclazole, and Thiabendazole are marketed for control of various agricultural pests. Another widely used thiazole derivative is the non-steroidal anti-inflammatory drug Meloxicam. The following anthroquinone dyes contain benzothiazole subunits: Algol Yellow 8 (CAS# [6451-12-3]), Algol Yellow GC (CAS# [129-09-9]), Indanthren Rubine B (CAS# [6371-49-9]), Indanthren Blue CLG (CAS# [6371-50-2], and Indanthren Blue CLB (CAS#[6492-78-0]). These thiazole dye are used for dying cotton.

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