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IUPAC names
Other names
2,3-Dihydro-1,3-thiazole or 4-thiazoline
2,5-Dihydro-1,3-thiazole or 3-thiazoline
4,5-Dihydro-1,3-thiazole or 2-thiazoline
504-79-0 (2,3) YesY
24576-55-4 (2,5) YesY
504-79-0 (4,5) YesY
Jmol 3D model (2,3): Interactive image
(2,5): Interactive image
(4,5): Interactive image
PubChem 151424 (2,3)
120269 (4,5)
Molar mass 87.14 g·mol−1
Appearance Colorless liquids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Thiazolines (or dihydrothiazoles) are a group of isomeric heterocyclic compound containing both sulfur and nitrogen in the ring. Although unsubstituted thiazolines are rarely encountered themselves, their derivatives are more common and some are bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.[1]


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

Related compounds[edit]

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[edit]

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.[3]

Thiazolines found in nature[edit]

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.[4]

See also[edit]


  1. ^ Walsh, Christopher T.; Nolan, Elizabeth M. (2008). "Morphing peptide backbones into heterocycles". Proceedings of the National Academy of Sciences USA. 105: 5655–5656. doi:10.1073/pnas.0802300105. 
  2. ^ Willstätter, Richard; Wirth, Theodor (1909). "Über Thioformamid". Chem. Ber. 42: 1908–1922. doi:10.1002/cber.19090420267. 
  3. ^ Gaumont, Annie-Claude; Gulea, Mihaela; Levillain, Jocelyne (2009). "Overview of the Chemistry of 2-Thiazolines". Chem. Rev. 109: 1371–1401. doi:10.1021/cr800189z. 
  4. ^ Agyemang, D.; Bardsley, K.; Brown, S.; Kraut, K.; Psota-Kelty, L.; Trinnaman, L. (2011). "Identification of 2-Ethyl-4-Methyl-3-Thiazoline and 2-Isopropyl-4-Methyl-3-Thiazoline for the First Time in Nature by the Comprehensive Analysis of Sesame Seed Oil". J. Food Sci. 76: C385–C391. doi:10.1111/j.1750-3841.2011.02071.x.