Production Method 1

83-53-4

3029-30-9

92616-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  12 h, 130 °C

Reference

Study on synthesis process of RDEA3170

Zhang, Xian-sheng; Liu, Yu-qiang; Xie, Ya-fei; Li, Chuan; Xin, Xiao; et al, Xiandai Yaowu Yu Linchuang, 2015, 30(10), 1179-1184

1,4-Dicyanonaphthalene Raw materials

• 1,4-Dibromonaphthalene

1,4-Dicyanonaphthalene Preparation Products

• 4-Bromonaphthalene-1-carbonitrile (92616-49-4)
• 1,4-Dicyanonaphthalene (3029-30-9)

• 1. Photochemical reaction between acenaphthene and arenecarbonitriles
  Enrico Boggeri,Elisa Fasani,Mariella Mella,Angelo Albini J. Chem. Soc. Perkin Trans. 2 1991 2097
• 2. Photochemically induced oxygenation of methylbenzenes, bibenzyls, and pinacols in the presence of naphthalene-1,4-dicarbonitrile
  Angelo Albini,Silvia Spreti J. Chem. Soc. Perkin Trans. 2 1987 1175
• 3. Synthetic studies on O-heterocycles via cycloadditions. Part 1. Photochemical (electron transfer sensitised) C-C cleavage of diaryloxiranes
  Paul Clawson,Patricia M. Lunn,Donald A. Whiting J. Chem. Soc. Perkin Trans. 1 1990 153
• 4. The electron transfer photochemistry of allenes with cyanoarenes. Photochemical nucleophile–olefin combination, aromatic substitution (photo-NOCAS) and related reactions
  Dino Mangion,Donald R. Arnold,T. Stanley Cameron,Katherine N. Robertson J. Chem. Soc. Perkin Trans. 2 2001 48
• 5. Direct determination of rate constants for coupling between aromatic radical anions and alkyl and benzyl radicals by laser-flash photolysis
  Torben Lund,Peter Christensen,Robert Wilbrandt Org. Biomol. Chem. 2003 1 1020

• Solvents and Organic Chemicals Organic Compounds cyanides/Cyanides
• Other Chemical Reagents

Professional Introduction to 1,4-Dicyanonaphthalene (CAS No. 3029-30-9)

1,4-Dicyanonaphthalene, with the chemical formula C₁₀H₂N₂, is a significant intermediate in organic synthesis and pharmaceutical chemistry. Its unique structure, featuring two cyano groups at the 1 and 4 positions of a naphthalene ring, makes it a versatile building block for various applications. This compound has garnered considerable attention in recent years due to its role in the development of advanced materials and biologically active molecules.

The CAS No. 3029-30-9 uniquely identifies this substance in scientific literature and industrial applications. Its molecular structure allows for facile functionalization, making it a valuable precursor in the synthesis of heterocyclic compounds, dyes, and specialty chemicals. The cyano groups introduce strong electron-withdrawing effects, which can be exploited in designing molecules with specific electronic properties.

In recent years, 1,4-dicyanonaphthalene has been explored for its potential in pharmaceutical research. The naphthalene core is a common motif in many bioactive compounds, and the introduction of cyano groups can enhance binding affinity to biological targets. For instance, studies have shown that derivatives of 1,4-dicyanonaphthalene exhibit promising activity as kinase inhibitors and antimicrobial agents. The electron-deficient nature of the cyano substituents facilitates interactions with metal ions and other functional groups, enabling the design of complex molecular architectures.

The compound's reactivity also makes it useful in polymer science. Researchers have utilized 1,4-dicyanonaphthalene to develop conductive polymers and organic semiconductors. The cyano groups can participate in polymerization reactions, leading to materials with tailored electrical properties. These polymers are of interest for applications in organic electronics, such as flexible displays and solar cells.

Another area where 1,4-dicyanonaphthalene has shown promise is in the synthesis of fluorescent probes. The naphthalene ring is known for its ability to emit light when excited, and the presence of cyano groups can modulate this emission. Such probes are valuable tools in bioimaging and diagnostics, allowing researchers to track biological processes with high sensitivity. Recent advancements have focused on tuning the fluorescence properties by introducing additional substituents or employing different solvents.

The industrial production of 1,4-dicyanonaphthalene typically involves the cyanation of naphthalene derivatives. Advances in catalytic methods have improved the efficiency and selectivity of these reactions, making it more feasible to produce high-purity material on an industrial scale. This has opened up new possibilities for large-scale applications in pharmaceuticals and materials science.

In conclusion, 1,4-dicyanonaphthalene (CAS No. 3029-30-9) is a multifaceted compound with broad utility across multiple scientific disciplines. Its unique structural features make it an indispensable tool for synthetic chemists and researchers working on advanced materials and drug discovery. As research continues to uncover new applications for this molecule, its importance is likely to grow further.

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