Cyclobutene

Cyclobutene

Names
Preferred IUPAC name Cyclobutene
Identifiers
CAS Number	822-35-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51206^Y
ChemSpider	63164^Y
ECHA InfoCard	100.011.360
EC Number	212-496-8
PubChem CID	69972
CompTox Dashboard (EPA)	DTXSID60231616
InChI InChI=1S/C4H6/c1-2-4-3-1/h1-2H,3-4H2^Y Key: CFBGXYDUODCMNS-UHFFFAOYSA-N^Y InChI=1/C4H6/c1-2-4-3-1/h1-2H,3-4H2 Key: CFBGXYDUODCMNS-UHFFFAOYAN
SMILES C\1=C\CC/1
Properties
Chemical formula	C4H6
Molar mass	54.092 g·mol^−1
Appearance	Colorless gas
Density	0.733 g/cm^3
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). Y verify (what is ^YN ?) Infobox references

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 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

• Cyclobutane
• Cyclobutadiene
• Cyclobutyne
• Squaric acid

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.