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Classification | Organic raw materials >> Nitrile compound |
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Name | 5,6-Bis[4-(dimethylamino)phenyl]-2,3-pyrazinedicarbonitrile |
Molecular Structure | ![]() |
Molecular Formula | C22H20N6 |
Molecular Weight | 368.43 |
CAS Registry Number | 888947-50-0 |
SMILES | CN(C)C1=CC=C(C=C1)C2=NC(=C(N=C2C3=CC=C(C=C3)N(C)C)C#N)C#N |
Density | 1.3±0.1 g/cm3 Calc.* |
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Boiling point | 550.7±50.0 ºC 760 mmHg (Calc.)* |
Flash point | 286.8±30.1 ºC (Calc.)* |
Index of refraction | 1.657 (Calc.)* |
* | Calculated using Advanced Chemistry Development (ACD/Labs) Software. |
The chemical substance 5,6-bis[4-(dimethylamino)phenyl]-2,3-pyrazinedicarbonitrile is a pyrazine derivative featuring two 4-(dimethylamino)phenyl substituents and two cyano groups, recognized in organic chemistry as a versatile compound, particularly in materials science and as a synthetic intermediate in pharmaceutical chemistry. Its discovery and applications are well-documented in the literature, rooted in the development of pyrazine-based chromophores and electron-deficient heterocycles. The origins of this compound are tied to the study of pyrazines, six-membered heterocycles with two nitrogen atoms, which have been explored since the 19th century for their presence in natural products and utility in synthesis. The introduction of aryl substituents and cyano groups to pyrazines gained prominence in the mid-20th century, driven by their electron-withdrawing properties and potential in electronic materials. The specific placement of 4-(dimethylamino)phenyl groups at the 5,6-positions and cyano groups at the 2,3-positions emerged in the late 20th century, fueled by the need for push-pull chromophores with strong electron donor-acceptor interactions for applications in nonlinear optics and organic electronics. Advances in cross-coupling reactions, such as Suzuki-Miyaura coupling, during the 1970s and 1980s enabled the precise synthesis of such functionalized pyrazines. Synthetically, 5,6-bis[4-(dimethylamino)phenyl]-2,3-pyrazinedicarbonitrile is typically prepared through a multi-step process. A common route starts with 2,3-dichloro-5,6-dicyanopyrazine, which is synthesized by chlorination of pyrazine-2,3-dicarbonitrile or its precursors. The 5,6-positions are then functionalized via Suzuki-Miyaura cross-coupling with 4-(dimethylamino)phenylboronic acid or its pinacol ester, using a palladium catalyst (e.g., Pd(PPh3)4) and a base like potassium carbonate. This step introduces the electron-donating dimethylaminophenyl groups, creating a donor-acceptor system with the electron-withdrawing cyano groups. Alternatively, the pyrazine core can be constructed via condensation of a diaminomaleonitrile derivative with a suitable diketone bearing the aryl substituents. These steps rely on well-established protocols in heterocyclic synthesis and cross-coupling chemistry, ensuring high yields and purity. The primary application of this compound is in materials chemistry, particularly as a push-pull chromophore in organic electronics and nonlinear optics. The 4-(dimethylamino)phenyl groups act as strong electron donors, while the 2,3-dicyanopyrazine core serves as an electron acceptor, creating a conjugated system with significant intramolecular charge transfer. This property makes the compound valuable for applications in organic light-emitting diodes (OLEDs), photovoltaic cells, and fluorescent sensors, where its strong absorption and emission in the visible spectrum are advantageous. In pharmaceutical chemistry, the compound serves as a synthetic intermediate, with the cyano groups providing handles for hydrolysis to carboxylic acids, reduction to amines, or cyclization to form heterocycles, enabling the synthesis of drug candidates like kinase inhibitors or receptor modulators. In academic research, the compound is used to study donor-acceptor interactions, photophysical properties, and pyrazine reactivity. Its synthesis has contributed to advancements in cross-coupling methodologies and the design of functional chromophores. The compound also finds use in developing molecular probes and dyes, leveraging its fluorescence and electronic properties. The significance of 5,6-bis[4-(dimethylamino)phenyl]-2,3-pyrazinedicarbonitrile lies in its role as a multifunctional chromophore and synthetic intermediate, combining the electron-deficient pyrazine core with strong donor-acceptor interactions. Its development reflects progress in heterocyclic synthesis and cross-coupling chemistry. By enabling applications in organic electronics, photonics, and pharmaceutical synthesis, it has become a critical tool in advancing materials and chemical research. References 2011. From Alkene-1,2-diamines. Science of Synthesis, 1. URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-041-00523 2011. Structure�Property Relationships and Nonlinear Optical Effects in Donor-Substituted Dicyanopyrazine-Derived Push�Pull Chromophores with Enlarged and Varied p-Linkers. European Journal of Organic Chemistry, 2012(2). DOI: 10.1002/ejoc.201101226 2012. CCDC 823673: Experimental Crystal Structure Determination. CCDC. DOI: 10.5517/ccwn33q |
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