1,3-Dioxo-1h-benzo[de]isoquinolin-2(3h)-yl trifluoromethanesulfonate
[CAS# 85342-62-7]

Identification

• Classification: Catalysts and additives >> Polymer
• Name: 1,3-Dioxo-1h-benzo[de]isoquinolin-2(3h)-yl trifluoromethanesulfonate
• Molecular Formula: C₁₃H₆F₃NO₅S
• Molecular Weight: 345.25
• CAS Registry Number: 85342-62-7
• EC Number: 893-422-7
• SMILES: C1=CC2=C3C(=C1)C(=O)N(C(=O)C3=CC=C2)OS(=O)(=O)C(F)(F)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 3077

Discovery and Applications

1,3-Dioxo-1H-benzo[de]isoquinolin-2(3H)-yl triflate, commonly known as naphthalimide triflate, is a highly active compound used in organic synthesis. Naphthalimide derivatives, including 1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl triflate, were generated from the exploration of isoquinoline and naphthyl compounds. Naphthalimide triflate combines a naphthalimide core with a triflate group. The triflate group is an excellent leaving group, making the compound highly reactive in nucleophilic substitution reactions. The naphthalimide core provides aromatic stability, allowing the compound to participate in a variety of chemical transformations.

The main function of naphthalimide triflate is as a versatile electrophile in organic reactions. Its triflate group facilitates nucleophilic substitution, allowing a variety of nucleophiles to be introduced to the naphthalimide core. This reactivity makes it useful for modifying and synthesizing complex organic molecules, especially in the formation of carbon-nitrogen and carbon-carbon bonds.

Naphthalimide triflate is used to introduce functional groups into organic molecules by nucleophilic substitution. This ability is crucial in the synthesis of complex molecules, allowing a variety of functional entities to be attached to the naphthalimide framework. It serves as a building block for the synthesis of various heterocyclic compounds and polymers, providing a pathway for the construction of complex molecular structures.

The compound is used in medicinal chemistry to synthesize bioactive molecules. Its reactivity can be used to create novel drugs with enhanced biological properties, including anticancer and antibacterial agents. Naphthalimide derivatives are used as fluorescent probes in biological research. The introduction of the triflate group enhances the solubility and functionality of these probes, facilitating their use in imaging and diagnostic applications.

In materials science, naphthalimide triflate is used to synthesize advanced polymers and materials. Its reactivity enables the incorporation of functional groups into the polymer backbone, thereby enhancing material properties. It is used in the production of dyes and pigments, where its structure contributes to the color properties and stability of the generated compounds.

Researchers use naphthalene diimide triflate to develop new synthetic methods. Its reactivity provides a platform for exploring innovative reactions and mechanisms in organic chemistry. The compound is studied for its potential role in catalytic processes, where it can act as a catalyst or catalyst precursor in various organic transformations.

References

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2005. Picosecond—nanosecond laser photolysis studies of a photoacid generator. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 4(1).
DOI: 10.1039/b411283k