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Thioacetone information


Thioacetone
Names
Preferred IUPAC name
Propane-2-thione[1]
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 Edit this at Wikidata
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 Putrid and intensely foul
Melting point −55°C(218.15k/-67°F)[2]
Boiling point 70°C(343.15k/158°F)[2]
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]

  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.
  2. ^ 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
  3. ^ V.C.E. Burnop; K.G. Latham (1967). "Polythioacetone Polymer". Polymer. 8: 589–607. doi:10.1016/0032-3861(67)90069-9.
  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.
  5. ^ Cite error: The named reference Derek Lowe was invoked but never defined (see the help page).

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