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Cyclobutene

Summary

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.[1] The compound was first prepared by thermolysis of the ammonium salt [C4H7N(CH3)3]OH (cyclobutyltrimethylammonium hydroxide).[2]

Cyclobutene
Names
Preferred IUPAC name
Cyclobutene
Identifiers
  • 822-35-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51206 checkY
ChemSpider
  • 63164 checkY
ECHA InfoCard 100.011.360 Edit this at Wikidata
EC Number
  • 212-496-8
  • 69972
  • DTXSID60231616 Edit this at Wikidata
  • InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2 checkY
    Key: CFBGXYDUODCMNS-UHFFFAOYSA-N checkY
  • InChI=1/C4H6/c1-2-4-3-1/h1-2H,3-4H2
    Key: CFBGXYDUODCMNS-UHFFFAOYAN
  • C\1=C\CC/1
Properties
C4H6
Molar mass 54.092 g·mol−1
Appearance Colorless gas
Density 0.733 g/cm3
Boiling point 2 °C (36 °F; 275 K)[1]
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

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.[3]

See also edit

References edit

  1. ^ a b 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.