2,3-Dicyanonaphthalene

Chemical Properties

beige fluffy powder

Uses

2,3-Naphthalenedicarbonitrile is a precursor to a molecular semiconductor. Dyes and metabolites.

Synthesis

2,3-Dicyanonaphthalene was prepared as follows:

Step 1. Synthesis of ,,','-tetrabromo o-xylene

250 ml of carbon tetrachloride, 6 ml of o-xylene (49.8 mmol) were measured in 500 ml of three-necked flask and heated to reflux, then added dropwise with 11 ml (199 mmol) of bromine, . At the same time, the reaction was irradiated with a 500 watt UV high-pressure mercury lamp, and the drop was completed in a few hours, and the light was continued to investigate the effects of drop time, drop rate of bromine, and UV light illumination time on the yield. Upon completion of the reaction, excess was evaporated from the reaction solution. Carbon tetrachloride, the remaining small amount of reaction solution was cooled, crystals were precipitated, filtered, and the refined product was recrystallized with trichloromethane to obtain white crystals.

Step 2, synthesis of 2,3-dicyanonaphthalene

Take 5g (11.9mmol) of ,,','-tetrabromo o-xylene, 1.6g (0.02mol) of fumononitrile, 25g (0.17mol) of iodinated naphthalene, 50 ml of anhydrous DMF, the mixture was heated at 75C . was heated at for several hours to examine the effect of reaction time on the yield. After completion of the reaction the product was cooled and then poured into 160 ml of ice-water mixture to obtain a dark red suspension, which was changed into a light yellow suspension by adding an appropriate amount, and filtered. into a light yellow suspension, filtration, precipitate washing, drying, recrystallization, the product is milky white needle-like crystals.