O-Ethyl thioacetate
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| IUPAC name
O-Ethyl ethanethioate
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| Other names
Ethyl thionacetate
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3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| C4H8OS | |
| Molar mass | 104.17 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.957 g/cm³ |
| Melting point | 105–109 °C (221–228 °F; 378–382 K) |
Refractive index (nD)
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1.4579 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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O-Ethyl thioacetate is an organosulfur compound with the formula C2H5OC(S)CH3. It is the unstable isomer of S-ethyl thioacetate.[1] It is prepared by treatment of the iminoester with hydrogen sulfide:[2]
- CH3C(=NH)OC2H5 + H2S → CH3C(=S)OC2H5 + NH3
The orthoester also reacts usefully with hydrogen sulfide in the presence of ferric chloride as a catalyst:[3]
- CH3C(OC2H5)3 + H2S → CH3C(=S)OC2H5 + 2 HOC2H5
Related compounds
- Ethyl thioacetate (C2H5SC(O)CH3) is the stable isomer of O-ethyl thioacetate.
References
- ^ Matthys J. Janssen (1969). "Thiolo, Thiono and Dithio Acids and Esters". In Saul Patai (ed.). Carboxylic Acids and Esters. PATAI's Chemistry of Functional Groups. New York: John Wiley. pp. 705–764. doi:10.1002/9780470771099.ch15. ISBN 978-0-471-66919-7.
- ^ Schmidt, Ulrich; Heymann, Ekkehard; Kabitzke, Karlheinz (1963). "Notiz zur verbesserten Darstellung von Thioncarbonsäureestern und deren Überführung in 1.2.3-Thiodiazole". Chem. Ber. 96 (5): 1478. doi:10.1002/cber.19630960545.
- ^ Ohno, A.; Koizumi, T.; Tsuchihashi, G. (1968). "A novel method to synthesize O-esters of thiocarboxylic acids". Tetrahedron Letters. 9 (17): 2083–2085. doi:10.1016/S0040-4039(00)89748-8.