4,5-Dichlorophthalonitrile

Chemical Properties

Off-white powder

Uses

4,5-Dichlorophthalonitrile is suitable as a reactant in the synthesis of 4,5-bis(3,4-dimethoxyphenyl) phthalonitrile and 4,5-bis(2,6-dimethoxyphenoxy) phthalonitrile. It may be used in the synthesis of 4,5-diphenoxyphthalonitrile.

General Description

4,5-Dichlorophthalonitrile (4,5-dichloro-1,2-dicyanobenzene) is a phthalonitrile derivative. It has been synthesized from 4,5-dichloro-1,2-benzenedicarboxamide and characterized by ¹H ,¹³C-NMR and IR. 4,5-dichlorophthalonitrile undergoes base catalyzed nucleophilic aromatic substitution reaction with O-, S- nucleophiles and acidic -CH containing compounds to form corresponding phthalonitrile derivatives, which are the precursors in the synthesis of phthalocyanines.

Synthesis

22.2 g of dichlorophthalic anhydride was added to 30 mL of formamide (HCONH2), and then refluxed at 200-220C for 3h, and then purified to obtain dichlorophthalimide; ii. 22.0 g of dichlorophthalimide obtained in step 1 was added to 538 mL of ammonia, and then stirred and reacted at room temperature for 48h, and then purified to obtain dichlorophthalic dicarboxamide; iii. 80 mL of N,N-dimethylformamide (DMF) and 58 mL of dichlorosulfoxide were mixed, and the mixture was obtained by stirring in an ice-water bath for 2h, and then 15.6g of dichlorophthalimide obtained in step II was added to the mixture, and continued to be stirred in an ice-water bath for 5h, and then left to stand for 18h, and then separated and purified by column chromatography, obtaining 4,5-dichlorophthalonitrile.