Thietane

Chemical compound From Wikipedia, the free encyclopedia

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2] Some derivatives are of interest as drugs.[3]

Quick facts Names, Identifiers ...
Thietane
Structural formula of thietane
Ball-and-stick model of the thietane molecule
Names
Preferred IUPAC name
Thietane
Systematic IUPAC name
Thiacyclobutane
Other names
Trimethylene sulfide
Identifiers
3D model (JSmol)
102383
ChEBI
ChemSpider
ECHA InfoCard 100.005.469 Edit this at Wikidata
EC Number
  • 206-015-0
UNII
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
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).
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Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.[4][5] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.[6]

Synthesis

Thietanes are the subject of many preparative studies.[7][8] They are traditionally produced in modest or poor yields from 1,3-difunctionalized alkanes.[9] One example is the reaction of trimethylene carbonate and potassium thiocyanate.[10]

C4H6O3 + KSCN → C3H6S + KOCN + CO2

An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.[11]

Br−(CH2)3−Br + Na2S → C3H6S + 2 NaBr

Reactions

Nucleophiles like butyllithium can open the ring in thietane.[12] Thietane also reacts with bromine.[13]

References

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