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Cyclobutene

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Cyclobutene
Names
Preferred IUPAC name Cyclobutene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.360 Edit this at Wikidata
EC Number
  • 212-496-8
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2Key: CFBGXYDUODCMNS-UHFFFAOYSA-N
  • InChI=1/C4H6/c1-2-4-3-1/h1-2H,3-4H2Key: CFBGXYDUODCMNS-UHFFFAOYAN
SMILES
  • C\1=C\CC/1
Properties
Chemical formula C4H6
Molar mass 54.092 g·mol
Appearance Colorless gas
Density 0.733 g/cm
Boiling point 2 °C (36 °F; 275 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cyclobutene is an organic compound with the chemical formula C4H6. It is a cycloalkene. It is a colorless gas that easily condenses. It is of interest in research but currently has no practical applications. A modern synthesis involves the 2-step dehydration of cyclobutanol. The compound was first prepared by thermolysis of the ammonium salt [C4H7N(CH3)3]OH (cyclobutyltrimethylammonium hydroxide).

Cyclobutene thermally isomerizes to 1,3-butadiene. This strongly exothermic reaction reflects the dominance of ring strain. In contrast, the corresponding equilibrium for hexafluorocyclobutene disfavors hexafluorobutadiene.

See also

References

  1. ^ J. Salaün; A. Fadel (1986). "Cyclobutene". Org. Synth. 64: 50. doi:10.15227/orgsyn.064.0050.
  2. Willstätter, R.; von Schmaedel, W. (1905). "Ueber einige Derivate des Cyclobutans". Chem. Ber. 38 (2): 1992–1999. doi:10.1002/cber.190503802130.
  3. David M. Lemal; Xudong Chen (2005). "Fluorinated Cyclobutanes and Their Derivatives". In Zvi Rappoport; Joel F. Liebman (eds.). The Chemistry of Cyclobutanes. PATAI'S Chemistry of Functional Groups. pp. 955–1029. doi:10.1002/0470864028.ch21. ISBN 0470864001.
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Cycloalkenes
Alkenes
Dienes
Trienes
Tetraenes
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