1,4-Dicyanobenzene

1,4-Dicyanobenzene
Names
	Preferred IUPAC name Benzene-1,4-dicarbonitrile
	Other names Terephthalonitrile; p-Dicyanobenzene
Identifiers
CAS Number	623-26-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3248224;
ChemSpider	11672;
ECHA InfoCard	100.009.804
EC Number	210-783-2;
PubChem CID	12172;
UNII	E6ITH5CIS3;
CompTox Dashboard (EPA)	DTXSID1060768;
	InChI InChI=1S/C8H4N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H Key: BHXFKXOIODIUJO-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1C#N)C#N;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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 LD₅₀ (rat, oral) is 6400 mg/kg.

References

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.
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.

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[1] 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.

[2] 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.

[3] 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.

[4] 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.