Thietane

Thietane
Structural formula of thietane
Ball-and-stick model of the thietane molecule
Names
IUPAC name
Thietane
Other names
Thiacyclobutane
Trimethylene sulfide
Identifiers
3D model (JSmol)
102383
ChemSpider
ECHA InfoCard 100.005.469
EC Number 206-015-0
UN number 1993
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 pictograms
GHS signal word DANGER
H225, H302
P210
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
4
2
1
Flash point -11(9) °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2]

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]

References

  1. ↑ Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2.07: 389–428. doi:10.1016/B978-008044992-0.00207-8.
  2. ↑ Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1.24: 773–802. doi:10.1016/B978-008096518-5.00024-1.
  3. ↑ Sievert, Thorbjörn; Laska, Matthias (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses. 41 (5): 399–406. PMID 26892309. doi:10.1093/chemse/bjw015.
  4. ↑ Brechbuhl, J; Moine, F; Klaey, M; Nenniger-Tosato, M; Hurni, N; Sporkert, F; Giroud, C; Broillet, MC (2013). "Mouse alarm pheromone shares structural similarity with predator scents". Proc. Natl. Acad. Sci. U.S.A. 110 (12): 4762–4767. PMC 3607058 Freely accessible. PMID 23487748. doi:10.1073/pnas.1214249110.
  5. ↑ Li, Shengju; Ahmed, Lucky; Zhang, Ruina; Pan, Yi; Matsunami, Hiroaki; Burger, Jessica L; Block, Eric; Batista, Victor S; Zhuang, Hanyi (2016). "Smelling sulfur: Copper and silver regulate the response of human odorant receptor OR2T11 to low molecular weight thiols". Journal of the American Chemical Society. in press: 13281–13288. PMID 27659093. doi:10.1021/jacs.6b06983.
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