3,5-Dinitrobenzenesulfonyl Chloride

[31206-25-4] C6H3ClN2O6S (MW 266.63) InChI = 1S/C6H3ClN2O6S/c7-16(14,15)6-2-4(8(10)11)1-5(3-6)9(12)13/h1-3H InChIKey = GSTCLLCEBJUOLB-UHFFFAOYSA-N (sulfonylating agent for the preparation of crystalline sulfonamides and sulfonate esters; 3,5-dinitrobenzenesulfonate esters exhibit high reactivity in solvolysis reactions1, 2) Physical Data: mp 98.5 °C. Solubility: sol AcOH, pyridine; insol diethyl ether. Form Supplied in: not commercially available; easily prepared. Preparative Method: by a modified Sandmeyer reaction.3, 4 Diazotization of 3,5-dinitroaniline (0.25 mol) at −15 °C in aqueous acetic acid/conc HCl followed by addition to a saturated solution of SO2 in acetic acid gives the product, which is precipitated by the addition of water, washed with water then diethyl ether, and dried under vacuum (81% yield). Handling, Storage, and Precautions: reactive sulfonylating agent: avoid contact with skin and mucous membranes. Can be stored at rt for prolonged periods when dried and kept free of moisture.