4-(Trifluoromethyl)thioanisole is an aromatic thio-ether that combines a lipophilic methylthio group with a strongly electron-withdrawing trifluoromethyl substituent at the para-position of the benzene ring. The title compound is a low-viscosity liquid with a characteristic mercaptan-like odour; it is miscible with most common organic solvents (dichloromethane, chloroform, ethyl acetate, THF, methanol) and displays limited hydrolytic sensitivity under neutral or mildly basic conditions.
Key physical data: density 1.25 g cm⁻³ (20 °C); refractive index n²⁰/D 1.509; flash point >90 °C; vapour pressure 0.3 mmHg (25 °C). The substance is stable indefinitely when stored in amber glass under an inert atmosphere at 2–8 °C.
Typical applications:
Versatile building block for the introduction of the lipophilic “SCF₃” motif into agro-chemical candidates and pharmaceutical intermediates; the SCF₃ group is metabolically robust and enhances membrane permeability.
Precursor to 4-(trifluoromethyl)benzenesulfonyl chloride via two-step oxidation/chlorination, itself a key reagent for the preparation of sulfonamide-based herbicides and HDAC inhibitors.
Internal standard for ¹⁹F-NMR quantitative analysis and reference material for environmental fate studies of trifluoromethylthio pollutants.
Hazard statement: Causes skin and eye irritation; harmful if inhaled. Use only in a well-ventilated area with appropriate PPE. SDS available on request.
