Thiazoline

Thiazoline

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Names
IUPAC name 4,5-dihydro-1,3-thiazole
Other names 4,5-Dihydrothiazole
Identifiers
CAS Number	504-79-0 Y
Jmol 3D model	Interactive image
PubChem	120269
SMILES C1CSC=N1
Properties
Chemical formula	C3H5NS
Appearance	colourless liquid
Boiling point	135 to 138 °C (275 to 280 °F; 408 to 411 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thiazoline is a heterocyclic compound containing both sulfur and nitrogen in the ring. Although thiazoline itself is rarely encountered, its derivatives are often bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.

Synthesis

Thiazolines were first prepared by dialkylation of thioamides. More commonly, they are prepared from derivatives of 2-aminoethanethiol (cysteamine).

File:2-Thiazoline, 3-Thiazoline und 4-Thiazoline.png

Isomeric heterocyclic compounds: 2-thiazoline, 3-thiazoline and 4-thiazoline (from left to right). R is an organyl residue.

Related compounds

Three related classes of C₃NS heterocycles are well studied, 1,3-thiazoles (parent: C₃H₃NS), 1,3-thiazolines (parent: C₃H₅NS), and 1,3-thiazolidines (parent: C₃H₇NS). The naming is analogous to the C3N2 heterocycles, imidazoles, imidazolines, and imidazolidines.

Substituted thiazolines

Many molecules contain thiazoline rings, one example being luciferin, the light-emitting molecule in fireflies. The amino acid cysteine is produced industrially from substituted thiazole.

Thiazolines found in nature

In a recent study, thiazolines were identified in nature through an analysis of sesame seed oil. The toasted sesame seed oil was extracted using a Solvent-Assisted Flavor Evaporation technique. The extract was analyzed by GC and GC-MS and a total of 87 components were identified. Amongst these components, 2-ethyl-4-methyl-3-thiazoline and 2-isopropyl-4-methyl-3-thiazoline were identified and confirmed as being present in a natural product for the first time.