Prop-2-ene-1-sulfonyl Chloride

[14418-84-9] C3H5ClO2S InChI = 1S/C3H5ClO2S/c1-2-3-7(4,5)6/h2H,1,3H2 InChIKey = AAHFRWRQQDVWPX-UHFFFAOYSA-N Alternate Name: allylsulfonyl chloride. Physical Data: colorless liquid, bp 74–75 °C/15 mmHg; nD251.4750.1 Solubility: prop-2-ene-1-sulfonyl chloride is soluble in various organic solvents and in water. In water, depending on the pH, this compound is hydrolyzed to the corresponding sulfonic acid or sulfonate.2 Preparative Methods: allylsulfonyl chloride is not commercially available, and various methods are described for its synthesis. The most common method consists of reacting allylbromide with sodium sulfite (aq. solution, 50–60 °C) to generate the corresponding sodium allylsulfonate that is further treated with phosphoryl chloride (120 °C). After hydrolysis of the excess phosphoryl chloride, the crude mixture is extracted with chloroform and the organic phase is dried and evaporated. Prop-2-ene-1-sulfonyl chloride is then distilled.1 A second procedure involves the treatment of allyltributyltin with sulfur dioxide, and the generated tributylstannyl prop-2-ene-1-sulfinate intermediate is then transformed to allylsulfonyl chloride by the addition of chlorine.3 The more recent way to synthesize allylsulfonyl chloride is the formation of a prop-2-ene-1-sulfinic acid·BCl3 complex from propene, sulfur dioxide, and boron trichloride in CH2Cl2 at −20 °C. The crude complex is then chlorinated by utilizing N-chlorosuccinimide to generate the desired prop-2-ene-1-sulfonyl chloride.4 Handling, Storage, and Precautions: prop-2-ene-1-sulfonyl chloride is a colorless stable liquid that can be stored over long period of time.