N ‐Chlorophthalimide

chemical structure image [3481‐09‐2] C 8 H 4 ClNO 2 (MW = 181.58) InChI = 1S/C8H4ClNO2/c9‐10‐7(11)5‐3‐1‐2‐4‐6(5)8(10)12/h1‐4H InChIKey = WDRFYIPWHMGQPN‐UHFFFAOYSA‐N (electrophilic chlorination reagent) Alternative Names: N‐ chlorphthalimid; 2‐chloro‐2 H ‐isoindole‐1,3‐dione; NCP. Physical Data: mp 181–183 °C. Solubility: slightly soluble in H 2 O, soluble in alcohols and ethers. Form Supplied in: white powder or crystals. Analysis of Reagent Purity: NCP can be characterized by HRMS, 1 H‐NMR, 13 C‐NMR. Preparative Method: general procedure for the synthesis of N ‐chlorophthalimide ( NCP ): a suspension of phthalimide (0.185 g, 1 mmol) in H 2 O (10 mL) was treated with trichloroisocyanuric acid ( TCCA ) (0.078 g, 0.33 mmol), and the mixture was stirred at rt for 1 h. Then the solid was collected by filtration, washed with H 2 O, and dried. Handling, Storage, and Precautions: store under refrigeration and protect from moisture; acutely irritating solid, with toxic effects similar to those of the free halogens; avoid inhalation; use an efficient fume hood; perform all operations as rapidly as possible to avoid extensive decomposition of the reagent.