N,N-Dibromobenzenesulfonamide andN,N-Dibromo-p-toluenesulfonamide

Abstract

N, N-Dibromobenzenesulfonamide [938-05-6] C6H5Br2NO2S (MW 314.98) InChI = 1S/C6H5Br2NO2S/c7-9(8)12(10,11)6-4-2-1-3-5-6/h1-5H InChIKey = OTVPURYEWXIAKH-UHFFFAOYSA-N (source of electrophilic bromine, oxidizing agent) Alternative Name: dibromamine-B. Physical Data: mp 110–111 °C (dec).1 Solubility: soluble in most common organic solvents;1 0.339 g/kg H2O (at 30 °C),1 160.6 g/kg glacial acetic acid (at 30 °C).1 Form Supplied in: yellow crystalline solid, not commercially available. Analysis of Reagent Purity: 1H (in d4-methanol) and 13C NMR (in CDCl3) data are available for comparison.1 Preparation: several high-yielding preparative methods have been described. The most common method is treatment of benzenesulfonamide with aqueous base (NaHCO32 or KOH3, 4) followed by the addition of liquid bromine. An alternative method involves the addition of liquid bromine to an aqueous solution of N-chlorobenzenesulfonamide (chloramine-B).1 Handling, Storage, Precautions: solutions decompose slightly when stored in colorless bottles exposed to light. For best results, solid N,N-dibromobenzenesulfonamide and its solutions should be stored in amber bottles.1 N,N-Dibromo-p-toluenesulfonamide [21849-40-1] C7H7Br2NO2S (MW 329.00) (cohalogenating agent, oxidizing reagent, electrophilic bromine source) Alternate Name: dibromamine-T. Physical Data: mp 79 °C.32 Solubility: soluble in most common organic solvents. Form Supplied in: crystalline solid and commercially not available.32 Analysis of Reagent Purity: 1H (in CDCl3), 13C NMR, and IR data are available for comparison.32 Preparative Method: the common method is treatment of 4-methylbenzenesulphonimide with a solution of NaOH in water followed by liquid bromine.32 The other method involves the treatment of chloramine-T with liquid bromine at room temperature.33 Handling, Storage, and Precautions: should be protected from light and stored in a cold dry place.