Methylenecyclohexane

Methylenecyclohexane
Names
	Preferred IUPAC name Methylidenecyclohexane
	Other names Methylenecyclohexane
Identifiers
CAS Number	1192-37-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	13846 ;
ECHA InfoCard	100.013.412
EC Number	214-752-4;
PubChem CID	14502;
UNII	ET4NT9H9LB ;
CompTox Dashboard (EPA)	DTXSID4061595 ;
	InChI InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h1-6H2 Key: YULMNMJFAZWLLN-UHFFFAOYSA-N ; InChI=1/C7H12/c1-7-5-3-2-4-6-7/h1-6H2 Key: YULMNMJFAZWLLN-UHFFFAOYAJ;
	SMILES C=C1CCCCC1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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

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.

References

^ Wittig, George; Schoellkopf, U. (1960). "Methylenecyclohexane". Organic Syntheses. 40: 66. doi:10.15227/orgsyn.040.0066.
^ 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.
^ 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

[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

[1]

[2]

[3]

Synthesis

Structure

See also

References