Ethyl thioacetate

S-Ethyl thioacetate
Names
	IUPAC name S-Ethyl ethanethioate
	Other names S-ethyl thioacetate, S-ethyl thiolacetate
Identifiers
CAS Number	625-60-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:179440;
ChemSpider	55117;
ECHA InfoCard	100.009.914
EC Number	210-904-9;
PubChem CID	61171;
CompTox Dashboard (EPA)	DTXSID5060807 ;
	InChI InChI=1S/C4H8OS/c1-3-6-4(2)5/h3H2,1-2H3 Key: APTGPWJUOYMUCE-UHFFFAOYSA-N;
	SMILES CCSC(=O)C;
Properties
Chemical formula	C4H8OS
Molar mass	104.17 g·mol−1
Appearance	colorless liquid
Density	0.971 g/cm³
Solubility in water	insoluble
Solubility	diethyl ether, ethanol
Refractive index (nD)	1.456-1.468
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H225, H302, H315, H318, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

S-Ethyl thioacetate is the organosulfur compound with the formula CH₃C(O)SC₂H₅. It is an ethyl ester of thioacetic acid. The compound is traditionally prepared by alkylation of potassium thioacetate and thiolation of acetyl chloride:^[1]

CH₃COSK + C₂H₅Br → CH₃C(O)SC₂H₅ + KBr

CH₃COCl + C₂H₅SH → CH₃C(O)SC₂H₅ + HCl

The compound has been well studied in part as a model for biologically relevant thioesters, such as Coenzyme A. H-D exchange of the methyl group has been examined in aqueous solution.^[2]

Related compounds

O-Ethyl thioacetate (C₂H₅OC(S)CH₃) is the unstable isomer of S-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.
^ Amyes, Tina L.; Richard, John P. (1992). "Generation and stability of a simple thiol ester enolate in aqueous solution". Journal of the American Chemical Society. 114 (26): 10297–10302. Bibcode:1992JAChS.11410297A. doi:10.1021/ja00052a028.

[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] Amyes, Tina L.; Richard, John P. (1992). "Generation and stability of a simple thiol ester enolate in aqueous solution". Journal of the American Chemical Society. 114 (26): 10297–10302. Bibcode:1992JAChS.11410297A. doi:10.1021/ja00052a028.

[1]

[2]