Monochlorocyclohexane

Monochlorocyclohexane is an organochlorine compound with the formula C6H11Cl. It consists of a cyclohexane ring bearing a single chlorine substituent, commonly referred to as chlorocyclohexane. Because the cyclohexane ring is symmetric, there is effectively one monosubstituted isomer for this structure, often described as 1-chlorocyclohexane. In the chair conformation, the chlorine can occupy axial or equatorial positions, and these conformers rapidly interconvert at room temperature.

Preparation methods include radical chlorination of cyclohexane, typically under photochemical conditions, which yields monochlorocyclohexane along with other chlorinated products. It can also be prepared by converting cyclohexanol to chlorocyclohexane using reagents such as thionyl chloride or by hydrohalogenation of cyclohexene with HCl, followed by purification to isolate the mono-chlorinated product.

Physical properties are characteristic of many chlorinated hydrocarbons: it is a colorless liquid or low-melting substance with limited water solubility and good solubility in many organic solvents. Its boiling point is relatively high for a C6 hydrocarbon, reflecting the presence of chlorine. It is flammable and should be handled in well-ventilated areas, away from sources of ignition.

Applications and occurrence: monochlorocyclohexane is used as an intermediate in organic synthesis and can serve as a solvent or building block in the manufacture of specialty chemicals, including agrochemicals, dyes, and pharmaceutical intermediates. It is typically produced and sold for laboratory and industrial chemical manufacturing, with handling practices that address its potential toxicity and environmental impact.

Safety considerations: exposure can irritate the skin, eyes, and respiratory tract; vapors may be harmful if inhaled. Proper protective equipment and ventilation are recommended, along with precautions to minimize environmental release.