Chemistry:1,4-Dicyanobenzene
From HandWiki
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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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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 pictograms | 
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, 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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Tracking categories (test):
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
The -1">50 (rat, oral) is 6400 mg/kg.
References
- ↑ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363.
- ↑ 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" (in en). Science 368 (6497): 1352–1357. doi:10.1126/science.aba3823. ISSN 0036-8075. PMID 32554592. Bibcode: 2020Sci...368.1352M. https://www.science.org/doi/10.1126/science.aba3823.
- ↑ 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" (in en). Angewandte Chemie International Edition 59 (47): 20890–20894. doi:10.1002/anie.202009819. ISSN 1433-7851. PMID 32767545. https://onlinelibrary.wiley.com/doi/10.1002/anie.202009819.
- ↑ 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" (in en). Journal of the American Chemical Society 144 (49): 22599–22610. doi:10.1021/jacs.2c08997. ISSN 0002-7863. PMID 36459170.
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