Trifluoromethanol
Trifluoromethanol is a synthetic organic compound with the formula. It is also referred to as perfluoromethanol or trifluoromethyl alcohol. The compound is the simplest perfluoroalcohol. The substance is a colorless gas, which is unstable at room temperature.
Synthesis
Trifluoromethanol eliminates hydrogen fluoride in an endothermic reaction and forms carbonyl fluoride.The equilibrium can be shifted toward trifluoromethanol at lower temperatures. If the synthesized trifluoromethanol is protonated by superacids, for example, the equilibrium can be further shifted to the left towards the desired product. Other primary and secondary perfluoroalcohols exhibit similar instability.
At temperatures in the range of −120 °C, trifluoromethanol can be prepared by treating trifluoromethyl hypochlorite with hydrogen chloride:
In this reaction, the recombination of a partially positively charged chlorine atom with a partially negatively charged chlorine atom is used as elemental chlorine. The undesired products, by-products chlorine, hydrogen chloride, and chlorotrifluoromethane, can be removed by evaporation at −110 °C. Trifluoromethanol has a melting point of −82 °C and a calculated boiling point of about −20 °C. The boiling point is thus about 85 K lower than that of methanol. This fact can be explained by the absence of intramolecular H—F bonds, which are also not visible in the infrared gas phase spectrum.
Trifluoromethoxide
Trifluoromethoxide is the conjugate base of trifluoromethanol. Installing the trifluoromethoxy group, trifluoromethoxylation, is a well developed theme in agricultural and medicinal chemistry.Solutions or trifluoromethoxide can be prepared by treating carbonyl fluoride with sources of fluoride ion, e.g. NaF):
Some trifluoromethylethers can be cleaved to release trifluoromethoxide.
Trifluoromethyl benzoate is a related source of the trifluoromethoxide ion.
In aqueous media, the decomposes at room temperature.