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Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators. It serves as a component of the vitamin thiamine (B1). It acts as a protected formyl group used in natural product synthesis. It reacts with alkyl lithium and Grignards reagent to prepare organometallic complexes. It is involved in the electrophilic aromatic substitution and nucleophilic aromatic substitution at C-5 and C-2 positions respectively. Further, it undergoes alkylation reaction to get thiazolium cation, which is used as a catalyst in the Stetter reaction and the Benzoin condensation. In addition to this, it is involved in the preparation of alagebrium.
For an example of 2-lithiation, see: J. Med. Chem., 37, 3492 (1994). For other uses of 2-lithiothiazole, see 2-Bromothiazole, A14838.
Li, F.; Meng, F.; Wang, Y.; Zhu, C.; Cheng, Y. Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+. Tetrahedron 2015, 71 (11), 1700-1704.
Mallia, C. J.; Englert, L.; Walter, G. C.; Baxendale, I. R. Thiazole formation through a modified Gewald reaction. Beilstein J. Org. Chem. 2015, 11, 875-883.
Gefahrenhinweise (EU): H225-H302-H319
Highly flammable liquid and vapour. Harmful if swallowed. Causes serious eye irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.