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

Josh Tibbetts; Alex Cresswell

doi:10.1002/047084289X.rn02513

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

Josh Tibbetts, Alex Cresswell

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Abstract

[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 language	English
Title of host publication	Encyclopaedia of Reagents for Organic Synthesis
Publisher	Wiley
Number of pages	10
ISBN (Electronic)	9780470842898
ISBN (Print)	9780471936237
DOIs	https://doi.org/10.1002/047084289X.rn02513
Publication status	Published - 13 Jan 2023

Publication series

Name	Encyclopedia of Reagents for Organic Synthesis (EROS)
Publisher	Wiley

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10.1002/047084289X.rn02513

4DPAIPN
This is the peer reviewed version of the following article: Tibbetts, J.D. and Cresswell, A.J. (2023). 1,3-Benzenedicarbonitrile, 2,4,5,6-Tetrakis(diphenylamino)-. In Encyclopedia of Reagents for Organic Synthesis which has been published in final form at https://doi.org/10.1002/047084289X.rn02513 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
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1 Active

Simplifying Amine Synthesis: New Strategies for Amine Activation (RS URF extension)
Cresswell, A. (PI)
The Royal Society
1/04/22 → 31/03/25
Project: Research council
A Radical Approach to C-H Alkylation
Cresswell, A. (PI)
Engineering and Physical Sciences Research Council
20/01/20 → 31/03/23
Project: Research council

Cite this

@inbook{49be6e81a2ce4ea7a6b23b2340f32800,

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

abstract = "[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.",

author = "Josh Tibbetts and Alex Cresswell",

year = "2023",

month = jan,

day = "13",

doi = "10.1002/047084289X.rn02513",

language = "English",

isbn = "9780471936237",

series = "Encyclopedia of Reagents for Organic Synthesis (EROS)",

publisher = "Wiley",

booktitle = "Encyclopaedia of Reagents for Organic Synthesis",

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TY - CHAP

T1 - 1,3-Benzenedicarbonitrile, 2,4,5,6-Tetrakis(diphenylamino)-

AU - Tibbetts, Josh

AU - Cresswell, Alex

PY - 2023/1/13

Y1 - 2023/1/13

N2 - [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.

AB - [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.

U2 - 10.1002/047084289X.rn02513

DO - 10.1002/047084289X.rn02513

M3 - Book chapter

SN - 9780471936237

T3 - Encyclopedia of Reagents for Organic Synthesis (EROS)

BT - Encyclopaedia of Reagents for Organic Synthesis

PB - Wiley

ER -

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

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Simplifying Amine Synthesis: New Strategies for Amine Activation (RS URF extension)

A Radical Approach to C-H Alkylation

Cite this