Phthalonitrile PHTHALONITRILE (1,2-DICYANOBENZENE) Benzene-1,2-dicarbonitrile~1,2-Dicyanobenzene
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Overview:
The aromatic nitrile compound phthalonitrile is a very important organic synthetic intermediate, widely found in medicine, pesticides, herbicides, insecticides, dyes, fragrances and natural products. For example, 2, 4-dinitro-6-cyano-aniline, which can be used to make excellent bright blue diazo dyes, and lemonitrile, an international new nitrile spice with sharp and strong lemon-like aroma.
Preparation:
Phthalonitrile is prepared as follows: Under the protection of argon, NiCl2·6H2O(0.05mmol, 11.9mg), dppf(0.06mmol, 33.3mg), Zn(0.2mmol, 13.0mg), DMAP(1.0mmol, 122.2mg) were added into the 25.0mL sealed tube successively. Zn(CN)2(0.8mmol, 93.9mg), p-chlorobanisole (1.0mmol, 140.6mg) and 2-chlorobenzonitrile (5.0mL) were then directly put into an oil bath at 60℃ for reaction. After 6h, the heating was stopped and the reaction liquid was cooled to room temperature. The reaction liquid was filtered directly through a short silica gel column, washed with dichloromethane and concentrated. Direct silica gel column chromatography purification (In view of the fact that most of the product is easy to be pumped away, in order to avoid mixing sample loss, unless special instructions, all samples are wet loading.) Eluent: petroleum ether/ethyl acetate = 3:1, the product was white solid phthalonitrile 106.1mg, the yield was 83%, the purity of 1HNMR was greater than 98%.
Production method:
Phthalimide reacts with ammonia to get phthalic acid amide, and then gets phthalonitrile by dehydration. In addition, the product can be prepared by ammoniating anhydride and then reacting with phosphorus oxytrichloride, or ammoxidation of naphthalenepentamine, or ammoxidation of o-xylene with ammonia.
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