Molecular Formula | C8H4N2O5 |
Molar Mass | 208.13 |
Density | 1.623±0.06 g/cm3 (20 ºC 760 Torr) |
Melting Point | 259 °C |
Boling Point | 347.31°C (rough estimate) |
Appearance | Solid |
pKa | 9.29±0.20(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.4900 (estimate) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
overview | 5-nitroindigo anhydride is a pharmaceutical intermediate, which can be prepared by nitration of indigo anhydride. 5-Nitroindigo anhydride can be used to prepare the muscle relaxant fluoroquinone. Fluoroquinone was first marketed in Japan in 1983 and developed by Japan's Tanabe Co., Ltd. After more than 20 years of clinical application, it has proved to be a relaxant with good curative effect on the face and neck muscle spasms. |
preparation | concentrated sulfuric acid (100mL) is added into a 250mL three-mouth flask, indigo anhydride (30.0g,0.18mol) is slowly added at 0-10 ℃ under mechanical stirring, 98% fuming nitric acid (14.2g,0.22mol) is added dropwise after stirring and dissolving, the temperature is maintained at 0-5 ℃, the dropwise addition is completed for 1h, and the reaction is continued for 1h, stop stirring, slowly pour the reaction solution into 300mL ice water mixture, stir for 20min, fully precipitate the solid, filter, wash with water, and dry to obtain 5-nitroindigo anhydride (37.0g, yield: 96.6%). m.p.263.8-265.3 ℃; The purity measured by HPLC is 97.2% (mobile phase is acetonitrile: 20mmol/L KH2PO4 aqueous solution (pH3.25)= 30:70,V/V). |