BENZYL AZIDE

Benzyl azide is used in the synthesis of 1,2,3-triazole derivatives. It serves as a reagent used to introduce a PhCH2N group into a molecule.

BENZYL AZIDE was used in the synthesis of stable 1,2,3-triazole derivatives.

Tetrahedron Letters, 16, p. 471, 1975 DOI: 10.1016/S0040-4039(00)71896-X
Journal of the American Chemical Society, 91, p. 4323, 1969 DOI: 10.1021/ja01043a071

Benzyl azide is an aromatic azide generally used in copper(I)-catalyzed azide-alkyne cycloaddition reactions.

A heat-sensitive explosive.Explosive reaction with bis(trifluoromethyl)nitroxide.Upon decomposition it emits toxic fumes of NOx. Seealso AZIDES.

Sodium azide (3.58 g, 55.0 mmol) was added to DMSO (120 mL) and stirred vigorously until fully dissolved. Benzyl bromide 168 (6.54 mL, 55 mmol) was added. The reaction mixture was stirred at RT overnight. The colourless liquid was worked up with water (100 mL), and extracted with diethyl ether (3 x 100 mL). The extractions were washed with water (2 x 80 mL) and brine (80 mL). The ether layer was dried over MgSO4 and after filtration, it was evaporated to dryness, giving benzyl azide 73 as a colourless oil (6.9 g, 51.8 mmol, 94%): IR (neat) νm a x / cm– 1 3455, 3028, 2970, 2946, 2093, 1605, 1586, 1496, 1454, 1349, 1252; 1H NMR (400 MHz, CDCl 3 ) δ 7.44 – 7.28 (m, 5H), 4.33 (s, 2H); 1 3C NMR (100 MHz, CDCl 3 ) δ 135.55, 129.05, 128.52, 128.44, 55.00.