Methylenecyclohexane

Methylenecyclohexane (IUPAC name: methylidenecyclohexane) is an organic compound with the molecular formula C7H12.

Methylenecyclohexane
Names
Preferred IUPAC name
Methylidenecyclohexane
Other names
Methylenecyclohexane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.412
EC Number
  • 214-752-4
UNII
  • InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h1-6H2 checkY
    Key: YULMNMJFAZWLLN-UHFFFAOYSA-N checkY
  • InChI=1/C7H12/c1-7-5-3-2-4-6-7/h1-6H2
    Key: YULMNMJFAZWLLN-UHFFFAOYAJ
  • C=C1CCCCC1
Properties
C7H12
Molar mass 96.170 g/mol
Boiling point 102 to 103 °C (216 to 217 °F; 375 to 376 K)
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

Synthesis

It can be produced by a Wittig reaction or a reaction with a Tebbe's reagent from cyclohexanone.[1][2][3] It can also be synthesized as a side product of the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene.

Structure

Methylenecyclohexane is an unsaturated hydrocarbon, containing a cyclohexane ring with a methylene (methylidine) group attached.

See also

References
  1. Wittig, George; Schoellkopf, U. (1960). "Methylenecyclohexane". Organic Syntheses. 40: 66. doi:10.15227/orgsyn.040.0066.
  2. Mark, Herman F. (2007). Encyclopedia of Polymer Science and Technology, Concise. Hoboken, New Jersey: John Wiley & Sons. p. 682. ISBN 978-0-470-04610-4. I this way, cyclohexanone is transformed into methylenecyclohexene and benzaldehyde into stryene.
  3. Dalton, David R. (August 4, 2011). Foundations of Organic Chemistry: Unity and Diversity of Structures, Pathways, and Reactions. John Wiley & Sons. pp. 819–820. ISBN 978-1-118-00538-5. Now, when cyclohexanone is added to the solution in which the [Tebbe] reagent has been generated, reaction occurs to produce methylenecyclohexane and triphenylphosphine oxide
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