Diazoaminobenzene (CAS NO.: ), which is also known as Triazene, 1,3-diphenyl-, could be produced through the following synthetic routes.

In a 5-l. flask fitted with a mechanical stirrer and a dropping funnel are placed 1 kg. of cracked ice, 1.5 l. of water, 279 g. (3 moles) of a technical grade of aniline, and 458 g. (388 cc., 4.5 moles) of concentrated hydrochloric acid (sp. gr. 1.18). The stirrer is started, and a solution of 109 g. (1.5 moles) of 95 per cent sodium nitrite in 250 cc. of water is added over a period of fifteen minutes. The reaction mixture is then stirred for fifteen minutes, and a solution of 422 g. (3.1 moles) of crystalline sodium acetate dissolved in 800 cc. of water is added over a period of five minutes. A yellow precipitate of diazoaminobenzene begins to form at once. Stirring is continued for forty-five minutes, keeping the temperature below 20°. The yellow diazoaminobenzene is filtered on a 19-cm. Büchner funnel, washed with 5 l. of cold water, and then sucked as dry as possible and spread out on a sheet of paper to dry. The product thus obtained is dissolved in 4 l. of boiling ligroin (b.p. 60–90°), filtered, and allowed to cool to room temperature and stand overnight. When crystallization is complete, the yellow crystals are filtered on a 19-cm. Büchner funnel, washed with 500 cc. of cold ligroin (b.p. 60–90°), and dried at room temperature. The yield of yellow crystals melting at 92–94° is 242–251 g. (82–85 per cent of the theoretical amount). If a product of greater purity is desired, the diazoaminobenzene is dissolved in 4 l. of boiling ligroin (b.p. 60–90°) and crystallized as before. The recrystallized diazoaminobenzene weighs 204–218 g. (69–73 per cent of the theoretical amount) and melts at 94–96°.