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We have successfully synthesized both enantiomers of a novel chiral ionic liquid, (R)- and (S)-[(3-chloro-2-hydroxypropyl) trimethylammonium][bis((trifluoromethyl)sulfonyl)amide] ((R)- and (S)-[CHTA]⁺[Tf₂N]^-) in optically pure form by a simple ion exchange reaction from corresponding chloride salts that are commercially available. In addition to the ease of preparation, this chiral IL has relatively high thermal stability (up to 300 °C), is liquid at room temperature (glass transition temperature of −58.4 °C), and exhibits strong enantiomeric recognition. The high solubility power and strong enantiomeric recognition ability make it possible to use this chiral IL to solubilize an analyte and to induce diastereomeric interactions for the determination of enantiomeric purity. In fact, we have successfully developed a novel method based on the near-infrared technique with this chiral IL serving both as solvent and as a chiral selector …