1,3-Oxathiolane
Chemical compound
From Wikipedia, the free encyclopedia
1,3-Oxathiolane is an organosulfur compound with the formula (CH2)3OS. It is a saturated five-membered heterocycle with non-adjacent S and O atoms. It is the parent of numerous derivatives. The parent compound is of little practical value, but there is some biotechnological interest in derivatives where one or more H atoms are replaced by other substituents.[1]
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| Names | |
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| Preferred IUPAC name
1,3-Oxathiolane | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C3H6OS | |
| Molar mass | 90.14 g·mol−1 |
| Appearance | colorless liquid |
| Density | 1.1779 g/cm3 |
| Boiling point | 127–129 °C (261–264 °F; 400–402 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and occurrence
The compound is prepared by condensation of mercaptoethanol with formaldehyde, as typical for synthesis of thioacetals.[2]
Derivatives
2-Methyl-4-propyl-1,3-oxathiane is a component of the flavor of passion fruit and other fruits.[3]
Apricitabine, a drug candidate containing a 1,3-oxathiane, is a nucleoside reverse transcriptase inhibitor.
Chemical structure of apricitabine
1,2-Oxathiolane
In contrast to the well-developed area of 1,3-oxathiolanes, 1,2-oxathiolane and its derivatives are not prevalent in the literature. The parent compound, which is derived from 3-mercaptopropanol, has been detected in solution [4] A bulky derivative has been characterized by X-ray crystallography.[5]