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Thietane

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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 Edit this at Wikidata
EC Number
  • 206-015-0
UN number 1993
  • InChI=1S/C3H6S/c1-2-4-3-1/h1-3H2 checkY
    Key: XSROQCDVUIHRSI-UHFFFAOYSA-N checkY
  • C1CSC1
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:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H302
P210
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
4
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).
☒N verify (what is checkY☒N ?)

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. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
  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. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
  3. ^ Sievert, Thorbjörn; Laska, Matthias (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses. 41 (5): 399–406. doi:10.1093/chemse/bjw015. PMID 26892309. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
  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. doi:10.1073/pnas.1214249110. PMID 23487748. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
  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. doi:10.1021/jacs.6b06983. PMID 27659093. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
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