1,4‐Dinitroimidazole

Abstract

[19182-81-1] C3H2N4O4 (MW 158.07) InChI = 1S/C3H2N4O4/c8-6(9)3-1-5(2-4-3)7(10)11/h1-2H InChIKey = HZPSREFSUPXCMN-UHFFFAOYSA-N (bioconjugation reagent for cysteine and lysine residues in peptides and proteins) Alternative Name: 1,4-dinitro-1H-imidazole. Physical Data: mp 92–94 °C; bp 433.7 ± 37.0 °C (predicted); d 4 20 = 2.01 ± 0.1 g cm−3 (predicted). Solubility: soluble in EA, CH2Cl2, CH3CN, MeOH, DMSO, DMF, and H2O. Form Supplied in: white or pale yellow solid. Analysis of Reagent Purity: IR, MS, and NMR. Preparative Methods: 4-nitroimidazole is prepared by mixing imidazole, 68% nitric acid, and 98% sulfuric acid at 50 °C in 98% yield (eq 1)1,2; 1,4-dinitroimidazole is prepared by mixing 4-nitroimidazole, glacial acetic acid, and 100% nitric acid at 17 °C in 67% (eq 2).1,2 (1) (2) Purification: crystallization from dichloromethane/petroleum ether or purified via column chromatography. Handling, Storage, and Precautions: stored in the dark at 4 °C. Be aware of the potential of 1,4-dinitroimidazole as an explosive.