1,4-Dicyanobenzene
Appearance
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Names | |
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Preferred IUPAC name
Benzene-1,4-dicarbonitrile | |
Other names
Terephthalonitrile; p-Dicyanobenzene
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.009.804 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H4N2 | |
Molar mass | 128.134 g·mol−1 |
Appearance | white solid |
Melting point | 224–227 °C (435–441 °F; 497–500 K) |
Hazards | |
GHS labelling: | |
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Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1] Hydrogenation of isophthalonitrile affords p-xylylenediamine.
1,4-dicyanobenzene is electrochemically active, forming a stable persistent radical at anodes.[2] For this reason, it has been used as a catalyst for automated reaction discovery, testing whether other species are redox active.[3][4]
Safety
[edit]The LD50 (rat, oral) is 6400 mg/kg.
References
[edit]- ^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 3527306730.
- ^ 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. 368 (6497): 1352–1357. Bibcode:2020Sci...368.1352M. doi:10.1126/science.aba3823. ISSN 0036-8075. PMID 32554592. S2CID 219842972.
- ^ 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. 59 (47): 20890–20894. doi:10.1002/anie.202009819. ISSN 1433-7851. PMID 32767545. S2CID 221076518.
- ^ 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. 144 (49): 22599–22610. doi:10.1021/jacs.2c08997. ISSN 0002-7863. PMC 9756344. PMID 36459170.