1,4-Dicyanobenzene Explained

1,4-Dicyanobenzene is an organic compound with the formula C6H4(CN)2. Two other isomers exist, phthalonitrile and isophthalonitrile. All three isomers are produced commercially by ammoxidation of the corresponding xylene isomers. 1,4-Dicyanobenzene is a colorless or white solid with low solubility in water. Hydrogenation of isophthalonitrile affords p-xylylenediamine.

1,4-dicyanobenzene is electrochemically active, forming a stable persistent radical at anodes.[1] For this reason, it has been used as a catalyst for automated reaction discovery, testing whether other species are redox active.[2] [3]

Safety

The (rat, oral) is 6400 mg/kg.

Notes and References

  1. Mo . Yiming . Lu . Zhaohong . Rughoobur . Girish . Patil . Prashant . Gershenfeld . Neil . Akinwande . Akintunde I. . Buchwald . Stephen L. . Jensen . Klavs F. . 2020-06-19 . Microfluidic electrochemistry for single-electron transfer redox-neutral reactions . Science . en . 368 . 6497 . 1352–1357 . 10.1126/science.aba3823 . 32554592 . 2020Sci...368.1352M . 219842972 . 0036-8075.
  2. Mo . Yiming . Rughoobur . Girish . Nambiar . Anirudh M. K. . Zhang . Kara . Jensen . Klavs F. . 2020-11-16 . A Multifunctional Microfluidic Platform for High-Throughput Experimentation of Electroorganic Chemistry . Angewandte Chemie International Edition . en . 59 . 47 . 20890–20894 . 10.1002/anie.202009819 . 32767545 . 221076518 . 1433-7851.
  3. Zahrt . Andrew F. . Mo . Yiming . Nandiwale . Kakasaheb Y. . Shprints . Ron . Heid . Esther . Jensen . Klavs F. . 2022-12-14 . Machine-Learning-Guided Discovery of Electrochemical Reactions . Journal of the American Chemical Society . en . 144 . 49 . 22599–22610 . 10.1021/jacs.2c08997 . 0002-7863 . 9756344 . 36459170.

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