6-Chloro-3-nitropyridine
2-Chloro-5-nitropyridine
CAS: 4548-45-2
Molecular Formula: C5H3ClN2O2
6-Chloro-3-nitropyridine - Names and Identifiers
| Name | 2-Chloro-5-nitropyridine |
| Synonyms | Chloro-5-nitropyrid 6-Chloro-3-nitropyridine 3-Nitro-6-chloropyridine 5-Nitro-2-chloropyridine 2-Chloro-5-nitropyridine 2-chloro-5-nitro-pyridin 2-Chloro-5-Nitro Pyridine |
| CAS | 4548-45-2 |
| EINECS | 224-908-3 |
| InChI | InChI=1/C5H3ClN2O2/c6-5-4(8(9)10)2-1-3-7-5/h1-3H |
| InChIKey | BAZVFQBTJPBRTJ-UHFFFAOYSA-N |
6-Chloro-3-nitropyridine - Physico-chemical Properties
| Molecular Formula | C5H3ClN2O2 |
| Molar Mass | 158.54 |
| Density | 1.6616 (rough estimate) |
| Melting Point | 105-108 °C (lit.) |
| Boling Point | 256.6±20.0 °C(Predicted) |
| Flash Point | 158°C |
| Water Solubility | Solubility in hot methanol. Insoluble in water. |
| Vapor Presure | 0.02mmHg at 25°C |
| Appearance | White crystal |
| Color | Light yellow to beige |
| BRN | 120453 |
| pKa | -4.22±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00006240 |
| Physical and Chemical Properties | Melting point 106-110°C |
| Use | Can be used in pharmaceuticals and other fine chemicals |
6-Chloro-3-nitropyridine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | US7175000 |
| HS Code | 29333990 |
| Hazard Class | IRRITANT |
6-Chloro-3-nitropyridine - Introduction
Insoluble in water
Last Update：2022-10-16 17:25:17
6-Chloro-3-nitropyridine - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Uses | 2-chloro-5-nitropyridine is an important fine chemical intermediate, which can be used to prepare a variety of drugs and pesticides such as antimalarial drugs. The drug, the fungicide cyclicidamide and some antibiotic drugs have a wide range of applications in the production of medicines and pesticides and have great production value. Can be used in pharmaceuticals and other fine chemicals |
| Preparation | A preparation method for preparing 2-chloro-5-nitropyridine using dichloride monoxide is to combine 3-nitropyridine with a molar ratio of 1-3 times the amount of alkali and 1-2 times the amount of chloride salt mixed with the solvent, and cooled to -15°C to -10°C at low temperature; after dissolving the molar ratio of 2-3 times the amount of dichloride monoxide in the solvent, under full stirring, dripping into the reaction mixture, maintaining -10°C to 0°C, after 2 hours of dripping, heating to room temperature and continuing to stir for 2 hours, until the raw material 3-nitropyridine is completely reacted, the reactant is poured into ice water, the organic layer is separated, the organic layer is collected, and the organic layer is washed once with hydrochloric acid with a mass concentration of 5%, wash once with water, dry anhydrous magnesium sulfate, and evaporate the organic solvent under reduced pressure to obtain 2-chloro-5-nitropyridine. |
| Production method | It is obtained by nitration, hydrolysis and chlorination of 2-aminopyridine. 1. Nitrification Add concentrated sulfuric acid to the reaction pot, add 2-aminopyridine at 50 ℃, and then add fuming nitric acid dropwise at 50 ℃. After addition, react at 45 ℃ for 2h and stir at room temperature for 4h. The reaction liquid is poured into crushed ice, and ammonia water is added below 5 ℃ to adjust to pH 6, and crystallization is precipitated. Filtration, drying, and recrystallization with water to obtain 2-amino-5-nitropyridine. 2. Hydrolysis Mix 2-amino -5-nitropyridine and 10% sodium hydroxide solution, heat boiling for 1h, hot filtration, filtrate cooling, and crystallization. Filter, mix the filter cake with water, add sulfuric acid to neutralize, filter, and dry to obtain 2-hydroxy-5-nitropyridine. 3. Chlorination The 2-hydroxy-5-nitropyridine, phosphorus oxychloride and dimethylformamide were mixed and refluxed for 2h. Cool and pour into crushed ice to precipitate crystals. Filter and dry to obtain the finished product. The total yield of nitrification, hydrolysis and chlorination is about 28%. |
Last Update：2024-04-09 15:16:50
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