1,4-Dicyanobenzene

1,4-Dicyanobenzene.svg 44 px Benzene-1,4-dicarbonitrile Terephthalonitrile; p-Dicyanobenzene 623-26-7 12172 11672 210-783-2 E6ITH5CIS3 3248224 747247 DTXSID1060768 1S/C8H4N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H BHXFKXOIODIUJO-UHFFFAOYSA-N C1=CC(=CC=C1C#N)C#N 8 4 2 white solid 224–227 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 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.10.1002/14356007.a17_363 Nitriles 2000 Pollak Peter Romeder Gérard Hagedorn Ferdinand Gelbke Heinz-Peter 3527306730 Hydrogenation of isophthalonitrile affords p-xylylenediamine. 1,4-dicyanobenzene is electrochemically active, undergoing reduction to form a persistent radical anion.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 https://www.science.org/doi/10.1126/science.aba3823 Science en 368 6497 1352–1357 10.1126/science.aba3823 32554592 2020Sci...368.1352M 219842972 0036-8075 registration For this reason, it has been used as a catalyst for automated reaction discovery, testing whether other species are redox active.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 https://onlinelibrary.wiley.com/doi/10.1002/anie.202009819 Angewandte Chemie International Edition en 59 47 20890–20894 10.1002/anie.202009819 32767545 221076518 1433-7851 subscription 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 It also has applications in photoredox catalysis as an organic photooxidant, as its singlet excited state has a high reduction potential, +2.55 relative to the saturated calomel electrode.Romero Nathan A. Nicewicz David A. Organic Photoredox Catalysis Chemical Reviews 14 September 2016 116 17 10075–10166 10.1021/acs.chemrev.6b00057 Safety The (rat, oral) is 6400 mg/kg. References Category:Benzonitriles