1,3-Benzenedicarbonitrile, 2,4,5,6-Tetrakis(diphenylamino)-

Josh Tibbetts, Alex Cresswell

Research output: Chapter or section in a book/report/conference proceedingChapter or section

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[1846598‐27‐3] C56H40N6 (MW 796.96) InChI = 1S/C56H40N6/c57‐41‐51‐53(59(43‐25‐9‐1‐10‐26‐43)44‐27‐11‐2‐12‐28‐44)52(42‐58)55(61(47‐33‐17‐5‐18‐34‐47)48‐35‐19‐6‐20‐36‐48)56(62(49‐37‐21‐7‐22‐38‐49)50‐39‐23‐8‐24‐40‐50)54(51)60(45‐29‐13‐3‐14‐30‐45)46‐31‐15‐4‐16‐32‐46/h1‐40H InChIKey = ZOMQCVKHGOMNER‐UHFFFAOYSA‐N (reagent used as an organic photoredox catalyst1) Alternative Names: 4DPAIPN, 2,4,5,6‐tetrakis(diphenylamino)‐1,3‐benzenedicarbonitrile, 2,4,5,6‐tetrakis(diphenylamino)isophthalonitrile, 1,3‐dicyano‐2,4,5,6‐tetrakis(N,N‐diphenylamino)benzene. Physical Data: absorption λmax = 405 nm,2 redox potentials (vs. SCE, saturated calomel electrode, as 0 V in CH3CN); −1.65 (P/P–), +0.90 (P*/P–), +1.03 (P+/P), −1.52 (P+/P*).3 Solubility: soluble in CH3CN, CHCl3, CH2Cl2, DMF, and DMSO; insoluble in H2O. Form Supplied in: yellow to yellow/brown solid. Preparative Methods: prepared via deprotonation of diphenylamine (5–6 equiv) in the presence of NaH (7–8 equiv) in DMF at 50–60 °C for 1 h, followed by the addition of 2,4,5,6‐tetrafluoroisophthalonitrile (1 equiv) in DMF and stirring at 40–50 °C for 4–16 h. Quenching with isopropanol/water causes the crude product to precipitate.2,3 Purification: recrystallization from CH2Cl2/pentane/hexanes; silica gel chromatography (eluting with CH2Cl2/hexanes). Handling, Storage, and Precautions: avoid contact with skin and eyes. Store in a cool, dry, and dark place.
Original languageEnglish
Title of host publicationEncyclopaedia of Reagents for Organic Synthesis
Number of pages10
ISBN (Electronic)9780470842898
ISBN (Print)9780471936237
Publication statusPublished - 13 Jan 2023

Publication series

NameEncyclopedia of Reagents for Organic Synthesis (EROS)


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