Methylcyclohexane

Methylcyclohexane

Names
IUPAC name methylcyclohexane
Other names Hexahydrotoluene Cyclohexylmethane Toluene hexahydride
Identifiers
CAS Number	108-87-2 Y
ChemSpider	7674 Y
Jmol 3D model	Interactive image
PubChem	7962
InChI InChI=1S/C7H14/c1-7-5-3-2-4-6-7/h7H,2-6H2,1H3 Y Key: UAEPNZWRGJTJPN-UHFFFAOYSA-N Y InChI=1/C7H14/c1-7-5-3-2-4-6-7/h7H,2-6H2,1H3 Key: UAEPNZWRGJTJPN-UHFFFAOYAG
SMILES CC1CCCCC1
Properties
Chemical formula	C7H14
Molar mass	98.19 g·mol−1
Appearance	Colourless liquid
Odor	faint, benzene-like
Density	0.77 g/cm3
Melting point	−126.3 °C (−195.3 °F; 146.8 K)
Boiling point	101 °C (214 °F; 374 K)
Solubility in water	Insoluble in water
Vapor pressure	37 mmHg (20°C)
Vapor pressure	{{{value}}}
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

Methylcyclohexane is an organic compound with the molecular formula is CH₃C₆H₁₁. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor. Methylcyclohexane is used as a solvent. It is mainly converted in naphtha reformers to toluene.

Production and use

It can be also produced by hydrogenation of toluene:

CH₃C₆H₅ + 3 H₂ → CH₃C₆H₁₁

Methylcyclohexane, as a component of a mixture, is usually dehydrogenated to toluene, which increases the octane rating of gasoline.

It is also one of a host substances in jet fuel surrogate blends, e.g., for Jet A fuel.

Solvent

Methylcyclohexane has no particular applications, although it used as an organic solvent, with properties similar to related saturated hydrocarbons such as heptane. B

Structure

Methylcyclohexane is a monosubstituted cyclohexane because it has one branching via the attachment of one methyl group on one carbon of the cyclohexane ring. Like all cyclohexanes, it can interconvert rapidly between two chair conformers. The lowest energy form of this monosubstituted methylcyclohexane occurs when the methyl group occupies an equatorial rather than an axial position. This equilibrium is embodied in the concept of A value. In the axial position, the methyl group experiences steric crowding (steric strain) because of the presence of axial hydrogen atoms on the same side of the ring (known as the 1,3-diaxial interactions). There are two such interactions, with each pairwise methyl/hydrogen combination contributing approximately 7.61 kJ/mol of strain energy. The equatorial conformation experiences no such interaction, and so it is the energetically favored conformation.

Flammability and toxicity

Like all hydrocarbons, methylcyclohexane is flammable.

Furthermore, it is considered "very toxic to aquatic life". Note, while methylcyclohexane is a substructure of 4-methylcyclohexanemethanol (MCHM), it is distinct in its physical, chemical, and biological (ecologic, metabolic, and toxicologic) properties.