Thioacetone

Thioacetone
Names
	Preferred IUPAC name Propane-2-thione
	Systematic IUPAC name Thiopropan-2-one
	Other names Propanethione; Thiopropanone; Thioacetone; Dimethyl thioketone; Sulfocarbon dimethanide; (Dimethyl)methylene sulfide; Sulfoacetone; Sulfopropanone;
Identifiers
CAS Number	4756-05-2 monomer; 828-26-2 trimer;
3D model (JSmol)	Interactive image;
ChemSpider	557043;
PubChem CID	641811;
CompTox Dashboard (EPA)	DTXSID70963875 ;
	InChI InChI=1S/C3H6S/c1-3(2)4/h1-2H3 Key: JTNXQVCPQMQLHK-UHFFFAOYSA-N; InChI=1/C3H6S/c1-3(2)4/h1-2H3 Key: JTNXQVCPQMQLHK-UHFFFAOYAT;
	SMILES CC(=S)C;
Properties
Chemical formula	C3H6S
Molar mass	74.14 g·mol−1
Appearance	Orange to brown liquid
Odor	Intensely sulfurous, leak-like
Melting point	−55°C(218.15k/-67°F)
Boiling point	70°C(343.15k/158°F)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Odor, skin irritant
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Thioacetone is an organosulfur compound belonging to the -thione group called thioketones with a chemical formula (CH₃)₂CS. It is an unstable orange or brown substance that can be isolated only at low temperatures.^[3] Above −20 °C (−4 °F), thioacetone readily converts to a polymer and a trimer, trithioacetone.^[4] It has an extremely potent, unpleasant odor, and is considered one of the worst-smelling chemicals known to humanity.^[5]

Thioacetone was first obtained in 1889 by Baumann and Fromm, as a minor impurity in their synthesis of trithioacetone.^[2]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 739. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ ^a ^b ^c William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73–103. doi:10.1007/3-540-07111-3_2
^ V.C.E. Burnop; K.G. Latham (1967). "Polythioacetone Polymer". Polymer. 8: 589–607. doi:10.1016/0032-3861(67)90069-9.
^ R.D. Lipscomb; W.H. Sharkey (1970). "Characterization and polymerization of thioacetone". Journal of Polymer Science Part A: Polymer Chemistry. 8 (8): 2187–2196. Bibcode:1970JPoSA...8.2187L. doi:10.1002/pol.1970.150080826.
^ Cite error: The named reference Derek Lowe was invoked but never defined (see the help page).

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 739. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[shar1979-2] William H. Sharkey (1979): "Polymerization through the carbon-sulfur double bond". Polymerization, series Advances in Polymer Science, volume 17, pages 73–103. doi:10.1007/3-540-07111-3_2

[V.C.E._Burnop,_K.G_1967,_Pages_589-3] V.C.E. Burnop; K.G. Latham (1967). "Polythioacetone Polymer". Polymer. 8: 589–607. doi:10.1016/0032-3861(67)90069-9.

[Lip-4] R.D. Lipscomb; W.H. Sharkey (1970). "Characterization and polymerization of thioacetone". Journal of Polymer Science Part A: Polymer Chemistry. 8 (8): 2187–2196. Bibcode:1970JPoSA...8.2187L. doi:10.1002/pol.1970.150080826.

[Derek_Lowe-5] Cite error: The named reference Derek Lowe was invoked but never defined (see the help page).

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