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| Names | |
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| IUPAC names 2,3-Dihydrothiazole 2,5-Dihydrothiazole 4,5-Dihydrothiazole | |
| 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 | |
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
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| Properties | |
| C3H5NS | |
| Molar mass | 87.14 g·mol−1 |
| Appearance | Colorless liquids |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Thiazolines (/θaɪˈæzoʊliːnz/; ordihydrothiazoles) are a group ofisomeric 5-memberedheterocyclic compounds containing bothsulfur andnitrogen in the ring. Although unsubstituted thiazolines are rarely encountered themselves, theirderivatives are more common and some are bioactive. For example, in a commonpost-translational modification, cysteine residues are converted into thiazolines.[1]
The name thiazoline originates from theHantzsch–Widman nomenclature.
Threestructural isomers of thiazoline exist depending on the position of the double bond. These forms do not readily interconvert and hence are nottautomers. Of these 2-thiazoline is the most common.
A fourth structure exists in which the N and S atoms are adjacent; this known asisothiazoline.
Thiazolines were first prepared by dialkylation ofthioamides byRichard Willstatter in 1909.[2] 2-Thiazolines are commonly prepared from 2-aminoethanethiols (e.g.cysteamine).[3] They may also be synthesized via theAsinger reaction.
Many molecules contain thiazoline rings, one example beingFirefly luciferin, the light-emitting molecule infireflies. The amino acidcysteine is produced industrially from substituted thiazole.[3]2-Aminothiazoline-4-carboxylic acid is an intermediate in the industrial synthesis of L-cysteine.[4]
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