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| | 2-Chloro-5-methyl-3-nitropyridine Basic information | | Application |
| | 2-Chloro-5-methyl-3-nitropyridine Chemical Properties |
| Melting point | 45-50 °C | | Boiling point | 290.8±35.0 °C(Predicted) | | density | 1.406±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | powder to crystal | | pka | -2.20±0.10(Predicted) | | color | White to Orange to Green | | Sensitive | Hygroscopic | | BRN | 138198 | | InChI | 1S/C6H5ClN2O2/c1-4-2-5(9(10)11)6(7)8-3-4/h2-3H,1H3 | | InChIKey | LUAJUWOJEFFNFE-UHFFFAOYSA-N | | SMILES | Cc1cnc(Cl)c(c1)[N+]([O-])=O | | CAS DataBase Reference | 23056-40-8(CAS DataBase Reference) |
| Hazard Codes | Xn,Xi | | Risk Statements | 36/37/38-21/22-41-37/38-22 | | Safety Statements | 36/37/39-26-36-39 | | RIDADR | 2811 | | WGK Germany | 3 | | Hazard Note | Harmful | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29333990 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 2-Chloro-5-methyl-3-nitropyridine Usage And Synthesis |
| Application | 2-Chloro-5-methyl-3-nitropyridine is an organic intermediate that can be obtained by chlorination of 5-methyl-3-nitropyridine-2(1H)-one. The chlorination reagent can be selected from phosphorus oxychloride. It can be used as an organic synthesis intermediate and a pharmaceutical intermediate, mainly in laboratory research and development processes and chemical production processes. | | Chemical Properties | Beige powder | | Synthesis | a) General procedure for the synthesis of 2-chloro-5-methyl-3-nitropyridine: 5-methyl-3-nitropyridin-2-ol (5 g, 32.4 mmol) and benzyltrimethylammonium chloride (3.01 g, 16.2 mmol) were dissolved in acetonitrile, followed by addition of phosphorochloridic acid (9.0 ml, 97.2 mmol). The reaction mixture was stirred at 80 °C for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water to quench the reaction. The aqueous phase was extracted with dichloromethane and the organic layers were combined, washed with saturated brine solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using dichloromethane as eluent. The fraction containing the target compound was collected and concentrated under reduced pressure to give 2-chloro-5-methyl-3-nitropyridine as a yellow solid (5.39 g, 97% yield). The product was confirmed by 1H-NMR (CDCl3, 300 MHz) and mass spectrometry (ESI): 1H-NMR δ= 8.45 (d, 1H, J = 2.3Hz), 8.04 (d, 1H, J = 2.3Hz), 2.46 (s, 3H); MS (ESI) m/z: 173.0 ([M+H]+). | | References | [1] Patent: US2011/28467, 2011, A1. Location in patent: Page/Page column 51
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 985 - 995
[3] Patent: EP2366691, 2011, A1. Location in patent: Page/Page column 9
[4] Patent: WO2015/73528, 2015, A1. Location in patent: Page/Page column 118
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 3504 |
| | 2-Chloro-5-methyl-3-nitropyridine Preparation Products And Raw materials |
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