Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2]
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Names | |||
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Preferred IUPAC name
Thietane | |||
Systematic IUPAC name
Thiacyclobutane | |||
Other names
Trimethylene sulfide | |||
Identifiers | |||
3D model (JSmol) |
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102383 | |||
ChEBI | |||
ChemSpider |
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ECHA InfoCard | 100.005.469 ![]() | ||
EC Number |
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PubChem CID |
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UNII | |||
UN number | 1993 | ||
CompTox Dashboard (EPA) |
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Properties | |||
C3H6S | |||
Molar mass | 74.14 g·mol−1 | ||
Appearance | Colourless liquid | ||
Odor | Sulfurous | ||
Density | 1.028 g cm−3 | ||
Boiling point | 94 to 95 °C (201 to 203 °F; 367 to 368 K) | ||
Hazards | |||
GHS labelling: | |||
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Danger | |||
H225, H302 | |||
P210 | |||
NFPA 704 (fire diamond) | |||
Flash point | -11(9) °C | ||
Related compounds | |||
Other anions |
Oxetane, Azetidine, Phosphetane | ||
Related compounds |
Thiirane, Dithietane, Tetrahydrothiophene, Thiane, Thiepane, Thiocane, Thionane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.[3][4] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.[5]
Thietane can be produced from the reaction of trimethylene carbonate and potassium thiocyanate, but the yield is low.[6]
An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.[7]
Nucleophiles like butyllithium can open the ring in thietane.[8] Thietane also reacts with bromine.[9]
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