Synthesis and structural characterization of 2,3-bis(hydroxymethyl)-2,3-dinitro-1,4-butanediol tetra p-toluenesulfonate

摘要

2,3-Bis(hydroxymethyl)-2,3-dinitro-1,4-butanediol tetra p-toluenesulfonate has been synthesized from nitromethane via condensation, cyclization, oxidative coupling, hydrolysis, and sulfonation. The total yield was 46.5 %. The structures of the title compound and intermediates were characterized by H-1 NMR, IR, and MS. X-ray single-crystal diffraction analysis revealed the title compound belongs to triclinic system; the space group is P-1. Mr = 856.89. The crystal cell data were: a = 11.341(2) nm, b = 13.743(3) nm, c = 14.845(3) nm, alpha = 104.69(3)A degrees, beta = 98.80(3)A degrees, gamma = 110.30(3)A degrees, V = 2023.7(9) nm(3), Z = 2, Dc = 1.406 g cm(-3), F(000) = 892, mu = 0.306 mm(-1), R = 0.0749, and wR (2) = 0.1893. Results from study of the thermal properties of the compound by DSC indicated its melting point and decomposition temperature were 400.25 and 510.70 K, respectively.