AzoMycin (2-NitroiMidazole)
2-Nitroimidazole
CAS: 527-73-1;36877-68-6
Molecular Formula: C3H3N3O2
AzoMycin (2-NitroiMidazole) - Names and Identifiers
| Name | 2-Nitroimidazole |
| Synonyms | Azomycin ro05-9129 2-nitro-imidazo 2-NITROMIDAZOLE 2-Nitroimidazole 2-Nitroimidaxole 2-nitro-1H-imidazole 1H-Imidazole, 2-nitro- 2-Nitroimidazole sulfate AzoMycin (2-NitroiMidazole) |
| CAS | 527-73-1 36877-68-6 |
| EINECS | 208-425-5 |
| InChI | InChI=1/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5) |
| InChIKey | YZEUHQHUFTYLPH-UHFFFAOYSA-N |
AzoMycin (2-NitroiMidazole) - Physico-chemical Properties
| Molecular Formula | C3H3N3O2 |
| Molar Mass | 113.07 |
| Density | 1.5988 (rough estimate) |
| Melting Point | 287 °C (dec.) (lit.) |
| Boling Point | 211.75°C (rough estimate) |
| Flash Point | 179.7°C |
| Water Solubility | insoluble |
| Solubility | NH4OH: soluble50mg/mL, clear, yellow to orange |
| Vapor Presure | 8.86E-06mmHg at 25°C |
| Appearance | Powder |
| Color | Light yellow to khaki-green |
| Merck | 14,921 |
| BRN | 116444 |
| pKa | 8.72±0.10(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.4264 (estimate) |
| MDL | MFCD00005185 |
| Physical and Chemical Properties | Melting point 287 ℃ (decomposition) |
| Use | Used as an intermediate in organic synthesis |
AzoMycin (2-NitroiMidazole) - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | NI7875000 |
| TSCA | Yes |
| HS Code | 29332990 |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 i.v. in mice: 80 mg/kg (Maeda) |
AzoMycin (2-NitroiMidazole) - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| background | malignant tumor is a common and frequently-occurring disease that seriously threatens human life. About 70% ~ 80% of tumor patients need radiotherapy. Radiosensitizers have received extensive attention in radiotherapy because they can improve the sensitivity of tumor cells to radiation. 2-Nitroimidazole is an important intermediate of sensitizing agents for various tumor radiotherapy, such as misonidazole (Misonidazole), pimonidazole (pimonidazole), etanidazole (etanidazole), etc. 2-nitroimidazole cannot be prepared by the direct nitration reaction of imidazole. The direct nitration of imidazole will give 4(5)-nitroimidazole, but not 2-nitroimidazole. |
| application | 2-nitroimidazole is the basic raw material for the synthesis and manufacture of nitroimidazole compounds in electrophilic radiosensitizers. N-substituted derivatives prepared from 2-nitroimidazole have been used as anti-tumor radiosensitizers in clinical studies. 2-Nitroimidazole is an important intermediate of sensitizing agents for various tumor radiotherapy, such as misonidazole (Misonidazole), pimonidazole (pimonidazole), etanidazole (etanidazole), etc. |
| preparation | 305g of imidazole ionic liquid is added into a clean and dry 1000ml reaction kettle, 304g of bromine is slowly added under stirring at 20 ℃, the reaction is exothermic, the temperature is controlled to be dropped at 20~30 ℃, and the drop is completed for about 0.5h to obtain reddish brown liquid. 136g imidazole is put into 5 batches, and the hydrogen bromide gas generated by the reaction is pumped out at 20~30 ℃ for 2.0h at the same time, and the discharged hydrogen bromide gas is absorbed with clear water. The reaction of the raw materials detected by liquid chromatography was complete. The reactants were extracted with toluene three times, 400ml of toluene was added each time, and the toluene extract was concentrated under reduced pressure to obtain 216.3g of 2-bromimidazole product. In a clean and dry 500L reaction kettle, 189g of dimethyl sulfoxide is added, 100g of 2-bromimidazole is added, 1g of cuprous iodide is added, 93.8g of sodium nitrite is added, the oil bath is slowly heated to 120 ℃, the temperature is kept for 8 hours, the temperature is reduced to 50 ℃ after the heat preservation is completed, 200g of water is added, and the crude product obtained after the ethyl acetate is concentrated is recrystallized with ethanol to obtain 52.3g of 2-nitroimidazole with a yield of 68.1%, the content is above 98.5%, and the melting point is 286~288 ℃. |
| use | intermediate of tumor radiotherapy sensitizer misonidazole (Misonidazole). The intermediate of the tumor radiotherapy sensitizer misonidazole (Misonidazole) is used as an intermediate in organic synthesis It is used to prepare nitroimidazole-substituted boric acid as a precursor for hypoxic tissue imaging. It is also used to prepare available site-selective radiosensitizers for estrogen receptor-rich tumors. |
| production method | mix aminoacetal S-methyl iso-sulfur and water evenly, stir and heat, evaporate to dry under reduced pressure, dissolve the residue with methanol, and then add acetone dropwise to obtain white crystalline N-(2, 2-diethoxyethyl) guanidine sulfate with a yield of 84.4%. N-(2, 2-diethoxyethyl) guanidine sulfate is mixed with concentrated hydrochloric acid, stirred, heated and refluxed, after the reaction, distilled water is added to evaporate to dry under reduced pressure, water is added to evaporate to dry, the residue is dissolved with absolute ethanol, and then anhydrous ether is added dropwise to obtain white solid 2-aminoimidazole with 64.5% yield. 2-Aminoimidazole, add fluoboric acid and water, cool to below -15 ℃, stir and drop sodium nitrate and water to form a solution. Add it and keep stirring. Pour the brown-green solution generated by the reaction into the copper sulfate pentahydrate solution, stir while adding, then add sodium nitrite to continue stirring, after the reaction, add concentrated hydrochloric acid to adjust the pH to 2, extract with acetate, and the extract After drying with anhydrous sodium sulfate, the ethyl acetate is recovered to the end, and the residue is recrystallized with ethanol to obtain 2-nitroimidazole. |
Last Update：2024-04-09 02:00:09
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View History
AzoMycin (2-NitroiMidazole)
2-(4-磺胺酰基苯基)乙酰胺
POLY[DIMETHYLSILOXANE-CO-METHYL(3-HYDROXYPROPYL)SILOXANE]-GRAFT-POLY(ETHYLENE GLYCOL) METHYL ETHER
phenoxy-aceticaci2-propenylester
RARECHEM AL BF 1228
3-{[(4-Isopropylbenzyl)oxy]methyl}piperidinehydrochloride
Isopropyl 4-Hydroxy
(R)-叔丁基3-氨基吡咯烷-1-羧酸酯盐酸盐
2-Phenyl-3-[[(4-chlorophenyl)ethynyl]thio]propan-2-ol
Methyl ester of 5-hexenoic acid
2-(4-磺胺酰基苯基)乙酰胺
POLY[DIMETHYLSILOXANE-CO-METHYL(3-HYDROXYPROPYL)SILOXANE]-GRAFT-POLY(ETHYLENE GLYCOL) METHYL ETHER
phenoxy-aceticaci2-propenylester
RARECHEM AL BF 1228
3-{[(4-Isopropylbenzyl)oxy]methyl}piperidinehydrochloride
Isopropyl 4-Hydroxy
(R)-叔丁基3-氨基吡咯烷-1-羧酸酯盐酸盐
2-Phenyl-3-[[(4-chlorophenyl)ethynyl]thio]propan-2-ol
Methyl ester of 5-hexenoic acid