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.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||98.189 g·mol−1|
|Melting point||−126.3 °C (−195.3 °F; 146.8 K)|
|Boiling point||101 °C (214 °F; 374 K)|
|0.014 g/l at 25 °C|
|Vapor pressure||37 mmHg (20°C)|
49.3 hPa at 20.0 °C
|Main hazards||severe fire hazard|
|Safety data sheet|||
|GHS signal word||Danger|
|H225, H304, H315, H336, H410|
|P210, P235, P301+310, P331, P370+378, P403|
|Flash point||−4 °C (25 °F; 269 K) Closed cup|
|283 °C (541 °F; 556 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|2250 mg/kg (mouse, oral)|
LC50 (median concentration)
|10172 ppm (mouse, 2 hr)|
10,000-12,500 ppm (mouse, 2 hr)
15227 ppm (rabbit, 1 hr)
|US health exposure limits (NIOSH):|
|TWA 500 ppm (2000 mg/m3)|
|TWA 400 ppm (1600 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production and useEdit
It can be also produced by hydrogenation of toluene:
- CH3C6H5 + 3 H2 → CH3C6H11
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 toxicityEdit
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.
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