Cyclohexanemethanol – general description and application

General description of Cyclohexanemethanol:

Cyclohexanemethanol (CM), or (hydroxymethyl)cyclohexane, or cyclohexylcarbinol [100-49-2] is six-membered alicyclic organic compound that belong to alcohols. In its pure form, it is colorless viscious highly flammable liquid with the boiling point of 179-180 °C.[1] It is insoluble in water and soluble in common organic solvents. CM is a non-corrosive and quick volatilize liquid with the LD50 = 250 mg/kg (mouse, intraperitoneal).[2]
Convenient laboratory preparation starts with chlorocyclohexane that is converted to cyclohexylmagnesium chloride, which reacts with formaldehyde or paraformaldehyde.[3]

Application of Cyclohexanemethanol:

Cyclohexanemethanol is usually used as a reagent in organic synthesis. It acts as a nucleohpile in highly beta-selective glucosidation of ethylthioglucosides.[4] It can be used as a starting material for the synthesis of cyclohexanecarboxaldehyde, cyclohexanecarboxylic acid, cyclohexanone, and 1,4-cyclohexadione by photocatalytic oxidation using titanium dioxide nanoparticles.[5] Cyclohexanemethanol can be biologically oxidized by the yeasts Candida maltosa and Trichosporon mucoides under laboratory conditions.[6]

Important Notes:

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible materials are Strong oxidizing agents, Acid chlorides, Acid anhydrides. Excess heat. Keep away from open flames, hot surfaces and sources of ignition. Hazardous Combustion Products: Carbon monoxide (CO), Carbon dioxide (CO2). Cyclohexanemethanol is stable under normal conditions

Product categorization (Chemical groups):

Main category:

Second level:


[1] H. Adkins, H. I. Cramer J. Am. Chem. Soc. 1930, 52, 4349.
[2] No author, National Technical Information Service. Vol. AD277-689
[3] H. Gilman, W. E. Catlin Org. Synth. 1926, 6, 22.
[4] Y. Okada, T. Mukae, K. Okajima, M. Taira, M. Fujita, H. Yamada Org. Lett. 2007, 9, 1573.
[5] O. S. Mohamed, S. A. Ahmed, M. F. Mostafa, A. M. A. Abdel-Wahab J. Photochem. Photobiol. A 2008, 209.
[6] R. Schlüter, A. Dallinger, J. Kabisch, I. Duldhardt, F. Schauer Appl. Microbiol. Biotechnol. 2019, 103, 4137.