Phthalimidosulfenyl Chloride

[54974-07-1] C8H4ClNO2S (MW 213.65) InChI = 1S/C8H4ClNO2S/c9-13-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H InChIKey = AQKMFIZDSMHXQR-UHFFFAOYSA-N (reacts as a pseudohalogen;1 synthetic equivalent of inaccessible sulfenyl chlorides;2-4 adds across double and triple bonds;2, 3, 5 reagent for the formation of episulfides;6 reacts with ketones to give β-keto sulfides7) Alternate Names: phthalimide-N-sulfenyl chloride; 1,3-dihydro-1,3-dioxo-2H-isoindole-2-sulfenyl chloride; N-(chlorothio)phthalimide. Physical Data: mp 115–117 °C. Solubility: sol chlorobenzene, benzene, CH2Cl2, MeOH; insol pentane. Form Supplied in: yellow crystals; not commercially available. Preparative Method: prepared by treatment of potassium phthalimide with S2Cl2 to form the disulfide which is then cleaved with chlorine in warm chloroform.1 Purification: recrystallization from methanol. Handling, Storage, and Precautions: can be stored at 0 °C for several months.