Molecular Formula | C7H6ClNO |
Molar Mass | 155.58 |
Density | 1.233 |
Melting Point | 35 - 37°C |
Boling Point | 238℃ |
Flash Point | 98℃ |
Solubility | Chloroform (Sparingly), Methanol (Slightly) |
Appearance | Solid |
Color | Off-White to Pale Yellow Low-Melting |
pKa | 1.06±0.10(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Hazard Class | IRRITANT |
Use | 1-(4-chloropyridine)-2-ethanone is an aromatic heterocyclic compound. Because its functional group contains halogen and carbonyl, it can react with other compounds very well, such as substitution reaction, affinity addition reaction, etc., and has good chemical activity, therefore, 1-(4-chloropyridine)-2-ethanone is a very important pharmaceutical intermediate. |
preparation | under the protection of nitrogen, 4-chloro-2-cyanopyridine (60g,0.42mol) and tetrahydrofuran (1000ml) are added into a 2L three-mouth bottle, stirred and dissolved, cooled to 0 ℃, add magnesium methyl iodide Grignard reagent (200ml 3M tetrahydrofuran solution, 0.6mmol) slowly in about 45 minutes. The initial system is transparent and dark solution, and the drop acceleration is adjusted at the later stage to make the temperature of the reaction liquid between 0-10 ℃. When all Grignard reagents are added, a green suspension is obtained, and the reaction is stirred at 0 ℃ for 2 hours. The reaction mixture was then added to ice water (1500ml). Add 2mol/L hydrochloric acid to adjust the pH value to 2, stir the mixture for another 15 minutes to stand and separate the liquid. The aqueous phase is extracted with ethyl acetate until TLC to detect no product. The organic phases were combined, washed once with saturated sodium chloride aqueous solution, dried with anhydrous Na2SO4, filtered, and the filtrate was distilled under reduced pressure in a rotary evaporator to remove all solvents to obtain 66g of crude yellow-brown oil product. The crude product was purified by column chromatography, combined with suitable fractions (characterized by TLC analysis). Remove the solvent to obtain the product 1-(4-chloropyridine)-2-ethanone (51g,0.32mol,76% yield), which is a transparent dark oil. |