Description
1-Propanesulfonyl chloride is a highly reactive sulfonyl chloride derivative that is highly hygroscopic. It is primarily used as a pharmaceutical intermediate or an organic synthesis reagent in the preparation of sulfonamide drugs, such as abrocitinib and vemurafenib.
Chemical Properties
Light yellow liquid
Uses
1-Propanesulfonyl chloride was used in synthesis of 1-alkyl-3-methylimidazolium alkanesulfonate ionic liquids.
Safety
1-Propanesulfonyl chloride is corrosive and irritating. Contact may cause severe skin burns and eye damage. Safety goggles and gloves must be worn when handling this substance.
Synthesis
2,4,6-Trichloro-[1,3,5]-triazine (TCT) was added at room temperature to a solution of propane-1-sulfonic acid in acetone dry, followed by NEt3 dropwise. The resulting mixture was irradiated to 80 °C (50 W of MW power) for 20 min in a sealed tube (10 mL pressure-rated reaction vial) in a self-tuning single-mode irradiating synthesizer. The mixture was cooled rapidly to room temperature by passing compressed air through the microwave cavity for 1 min. After cooling to room temperature, the precipitate was filtered off on Celite to afford 1-Propanesulfonyl chloride[1].
References
[1] Lidia De Luca, Giampaolo Giacomelli. “An Easy Microwave-Assisted Synthesis of Sulfonamides Directly from Sulfonic Acids.” The Journal of Organic Chemistry 73 10 (2008): 3967–3969.
