2446-83-5

19740-72-8

2446-83-5

General procedure for the synthesis of diisopropyl azodicarboxylate from diisopropyl hydrazine-1,2-dicarboxylate: Hydrazine hydrate (200 mg, 4.0 mmol), tetrahydrofuran (10 mL), and sodium carbonate (551 mg, 5.2 mmol) were added to a 30 mL round-bottomed flask, and isopropyl chlorocarbonate (980 mg, 8.0 mmol) was added dropwise, slowly, and under ice bath cooling. After the dropwise addition, the reaction was continued for 1 hour. Upon completion of the reaction, the solid insoluble material was removed by filtration and the filtrate was concentrated to about 90% of the original volume to give a tetrahydrofuran solution of diisopropyl 1,2-hydrazinedicarboxylate. Toluene (10 mL) was added to this solution, and the remaining tetrahydrofuran was removed by concentration to obtain a toluene solution of diisopropyl 1,2-hydrazinedicarboxylate. Subsequently, pyridine (316.4 mg, 4.0 mmol) and additional toluene (10 mL) were added to this toluene solution, and the reaction was carried out by slowly adding N-bromosuccinimide (711.9 mg, 4.0 mmol) at 20 °C for 2 hours. At the end of the reaction, the reaction solution was washed with water (3 mL x 2), dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was purified by distillation to give diisopropyl azodicarboxylate as a clarified liquid (628.5 mg, 77.8% yield).