3,6-Diphenyl-1,2,4,5-tetrazine

Abstract

[6830-78-0] C14H10N4 (MW 234.28) InChI = 1S/C14H10N4/c1-3-7-11(8-4-1)13-15-17-14(18-16-13)12-9-5-2-6-10-12/h1-10H InChIKey = XAUWSIIGUUMHQQ-UHFFFAOYSA-N (an electron-deficient heteroaromatic azadiene capable of participation in inverse electron demand cycloaddition reactions with a wide range of dienophiles1) Alternate Name: diphenyl-sec-tetrazine. Physical Data: red, purple powder; mp 196–198° C.17a Solubility: soluble in most organic solvents (such as CH2Cl2) Form Supplied in: red, purple powder. Analysis of Reagent Purity: 1H13C NMR, mp, and elemental analysis.17 Preparative Method: 3,6-diphenyl-1,2,4,5-tetrazine is prepared by the reaction of 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazene with glacial acetic acid and aqueous solution of sodium nitrite (3 equiv). Intermediate 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazene is in turn prepared by refluxing elemental sulfur, benzonitrile (1.5 equiv), and hydrazine monohydrate (3 equiv) in ethanol (eq 15)17b Purification: recrystallization from CHCl3 or column chromatography (silica gel, hexanes/EtOAc, 4:1) yields red purple needles. Handling, Storage, and Precautions: 3,6-diphenyl-1,2,4,5-tetrazine is stable and of unknown adverse effects and 3,6-diphenyl-1,4-dihyro-1,2,4,5-tetrazines is stable; however, if left exposed to air, it is slowly oxidized to 3,6-diphenyl-1,2,4,5-tetrazine.