3-[3-(Trifluoromethyl)phenyl]propionitrile

Updated: 2026-08-05

Overview

3-[3-(Trifluoromethyl)phenyl]propionitrile is an organic compound featuring a phenyl ring substituted with a trifluoromethyl group and a propionitrile side chain. It is widely used as a versatile intermediate in pharmaceuticals and agrochemicals due to its reactive nitrile functionality and trifluoromethyl group, which enhances lipophilicity and metabolic stability in bioactive molecules. This compound is synthesized through nucleophilic substitution or cyanoethylation reactions involving 3-(trifluoromethyl)benzyl derivatives. Its commercial availability and stability make it a preferred choice for industrial applications requiring fluorinated aromatic nitriles.

Physical and Chemical Properties

The compound is a colorless to pale yellow liquid with a density of approximately 1.22 g/cm³ and a boiling point of 280-282°C. It is soluble in common organic solvents like ethanol and acetone but exhibits negligible solubility in water, typical of aromatic nitriles. Key chemical properties include the reactivity of the nitrile group, which participates in hydrolysis, reduction, and cycloaddition reactions. The electron-withdrawing trifluoromethyl group further activates the aromatic ring for electrophilic substitutions, making it valuable for derivatization.

Main Applications

3-[3-(Trifluoromethyl)phenyl]propionitrile serves as a critical intermediate in synthesizing active pharmaceutical ingredients (APIs), particularly for CNS drugs and anti-inflammatory agents. Its trifluoromethyl group improves drug bioavailability and resistance to enzymatic degradation. In agrochemicals, it is used to produce herbicides and fungicides. The compound also finds niche applications in material science, such as liquid crystal formulations, where fluorinated aromatic compounds enhance thermal stability.

Safety and Storage

The compound is classified as harmful (H302/H312/H332) and requires handling with gloves, goggles, and fume hoods. Inhalation or skin contact can cause irritation, and ingestion may lead to systemic toxicity. Storage recommendations include keeping the material in tightly sealed containers under inert atmospheres (e.g., nitrogen) to prevent moisture absorption and degradation. Compatibility with metals and plastics should be verified for long-term storage.

B2B Procurement Guide

Buyers should prioritize suppliers who provide detailed certificates of analysis (CoA) specifying purity (≥98%), water content, and residual solvents. Bulk procurement (25 kg drums) typically reduces costs by 10-20% compared to smaller quantities. Due to regulatory scrutiny on fluorinated compounds, ensure suppliers comply with REACH or TSCA regulations. Sample testing via HPLC or GC-MS is advisable to confirm identity and purity before large-scale orders.