Molecular Formula | C6H5ClN2O2 |
Molar Mass | 172.57 |
Density | 1.5610 (rough estimate) |
Melting Point | 70-74 °C |
Boling Point | 200°C (rough estimate) |
Flash Point | 108.5°C |
Solubility | soluble in Methanol |
Vapor Presure | 0.0255mmHg at 25°C |
Appearance | Solid |
Color | Brown |
pKa | -1?+-.0.10(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.5500 (estimate) |
MDL | MFCD03085820 |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
HS Code | 29349990 |
Introduction | 2-chloro-3-nitro-6-methylpyridine is an organic intermediate, 2-amino-3-nitro-6-methylpyridine can be obtained by first nitration from 2-amino-6-methylpyridine, the diazotization reaction then yields 2-hydroxy-3-nitro-6-methylpyridine and, finally, 2-chloro-3-nitro-6-methylpyridine. 2-chloro-3-nitro-6-methylpyridine can be used in the preparation of 2-phenylpyridine and 2-(4-dibenzofuran)-pyridine. |
preparation | 2-hydroxy-3-nitro-6-methylpyridine (I-a) add 152 ml of concentrated sulfuric acid slowly to the reaction flask containing 1.4g (1.47mol) of 2-hydroxy-6-methylpyridine. After addition, 92mL (mol) is added dropwise at room temperature . Fuming nitric acid. The droplet acceleration was controlled so that the internal temperature was lower than 60 °c. After dropping, the mixture was stirred at room temperature for 1hr. The reaction solution was poured into ice water to precipitate a solid and filtered. The pH value of the filtrate was adjusted to 5-6 with sodium carbonate, and solid was precipitated and suction filtered. The solid was washed with anhydrous ethanol, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, and the solvent was recovered under reduced pressure. 120g (56%) of a yellow solid was obtained after drying. (Not separated, directly to the next reaction) 2-chloro-3-nitro-6-methylpyridine (I-b) 120g (0.8mol) of the above mixture, 400ml of phosphorus oxychloride and 200ml of toluene were added to the reaction flask, mechanically stirred and warmed to reflux. TLC tracking, 6hrs after the disappearance of raw materials. Excess phosphorus oxychloride and toluene were recovered under reduced pressure, and the residual paste was poured into ice water, and the pH value was adjusted to 8-9 by sodium hydroxide aqueous solution. Ethyl acetate 200mL × 5 extraction, combined organic phase, decompression back solvent. The crude product was subjected to column chromatography (developing solvent: ethyl acetate: petroleum ether = 1: 40) to obtain 2-chloro-3-nitro-6-methylpyridine light yellow 45g of solid (yield: 33%),mp:58~60. |