tetrakis(9H-carbazol-9-yl)benzene-1,3-dicarbonitrile

EN300-6487157

Product class

Building Blocks

CAS number

1416881-52-1

MW

788.90

Purity

95%

Stock Availability

EU, US, DE, UA

Lead time

1-5 days delivery time

Ligang for organic photocatalysis

2,4,5,6-Tetra(carbazol-9-yl)isophthalonitrile also known as 4CzIPN is a donor-acceptor chromophore and efficient metal-free photoredox catalyst for organic synthesis[1]. The compound exists as a powder, that is stable in the fridge for an extended period and easy to handle[2]. It is a popular catalyst in photoredox/Ni dual catalytic C(sp3)−C(sp2) cross-coupling where 4CzIPN demonstrates exceptional efficacy in arylation of a wide scope of substrates[3], [4]. It enables amine alpha-arylation, α-amino acid decarboxylation-arylation, and trifluoroborate arylation with good yields, utilizing only a catalytic amount of the 4CzIPN[3], [4], [5]. Importantly, this process can be performed under soft conditions without the need for strong UV irradiation and even with blue LED light[1], [5].

Synonyms: 4CzIPN; 2,4,5,6-Tetra(carbazol-9-yl)isophthalonitrile; 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile

1. Organic Photoredox Catalysis. Romero N. A.; Nicewicz D. A. Chem Rev 2016, 116 (17), 10075–10166. DOI: 10.1021/acs.chemrev.6b00057 2. 1,3-Benzenedicarbonitrile, 2,4,5,6-Tetra-9 H -Carbazol-9-Yl-. Lu J.; Gui R.; Zhang J. Encyclopedia of Reagents for Organic Synthesis 2017, 1–2. DOI: 10.1002/047084289X.rn02068 3. Single-Electron Transmetalation in Organoboron Cross-Coupling by Photoredox/Nickel Dual Catalysis. Tellis J. C.; Primer D. N.; Molander G. A. Science 2014, 345 (6195), 433–436. DOI: 10.1126/science.1253647 4. Merging Photoredox with Nickel Catalysis: Coupling of α-Carboxyl Sp3-Carbons with Aryl Halides. Zuo Z.; Ahneman D. T.; Chu L.; Terrett J. A.; Doyle A. G.; MacMillan D. W. C. Science 2014, 345 (6195), 437–440. DOI: 10.1126/science.1255525 5. Donor–Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(Sp3)–C(Sp2) Cross-Coupling. Luo J.; Zhang J. ACS Catal 2016, 6 (2), 873–877. DOI: 10.1021/acscatal.5b02204

Name:

tetrakis(9H-carbazol-9-yl)benzene-1,3-dicarbonitrile

SMILES:

N#CC=1C(=C(C#N)C(=C(C1N2C3=CC=CC=C3C4=CC=CC=C42)N5C6=CC=CC=C6C=7C=CC=CC75)N8C9=CC=CC=C9C=%10C=CC=CC%108)N%11C%12=CC=CC=C%12C=%13C=CC=CC%13%11

CAS number:

1416881-52-1

Product class:

Building Blocks

ACD number:

MFCD27939633

CLogP:

16.956

Class:

Lab Reagents

Formula:

C₅₆H₃₂N₆

Subclass:

Nitriles

MW:

788.90