O-Ethyl thioacetate

O-Ethyl thioacetate
Names
	IUPAC name O-Ethyl ethanethioate
	Other names Ethyl thionacetate
Identifiers
CAS Number	926-67-0 ;
3D model (JSmol)	Interactive image ;
ChemSpider	120473 ;
PubChem CID	926-67-0 ;
CompTox Dashboard (EPA)	DTXSID10239066 ;
	InChI InChI=1S/C4H8OS/c1-3-5-4(2)6/h3H2,1-2H3 Key: IEPFHYMMMGMRNF-UHFFFAOYSA-N;
	SMILES CCOC(=S)C;
Properties
Chemical formula	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)	1.4579
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated November 25, 2025

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.

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[PATAI-1] 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.

[2] 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.

[3] 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.

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[2]

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Names

IUPAC name O-Ethyl ethanethioate
Other names Ethyl thionacetate
Identifiers
CAS Number	926-67-0
3D model (JSmol)	Interactive image
ChemSpider	120473
PubChem CID	926-67-0
CompTox Dashboard (EPA)	DTXSID10239066
InChI InChI=1S/C4H8OS/c1-3-5-4(2)6/h3H2,1-2H3 Key: IEPFHYMMMGMRNF-UHFFFAOYSA-N
SMILES CCOC(=S)C
Properties
Chemical formula	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 (n_D)	1.4579
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references