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4,5,6,7-Tetrafluoro-1H-isoindole-1,3(2H)-dione
[CAS# 652-11-9]

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Identification
Classification Organic raw materials >> Heterocyclic compound >> Indoles
Name 4,5,6,7-Tetrafluoro-1H-isoindole-1,3(2H)-dione
Synonyms Tetrafluorophthalimide
Molecular Structure CAS # 652-11-9, 4,5,6,7-Tetrafluoro-1H-isoindole-1,3(2H)-dione, Tetrafluorophthalimide
Molecular Formula C8HF4NO2
Molecular Weight 219.09
CAS Registry Number 652-11-9
EC Number 667-801-0
SMILES C12=C(C(=C(C(=C1F)F)F)F)C(=O)NC2=O
Properties
Solubility Slightly soluble (6.8 g/L) (25 ºC), Calc.*
Density 1.761±0.06 g/cm3 (20 ºC 760 Torr), Calc.*
Melting point >250 ºC**
* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)
** Iglesias, Rodrigo S.; Journal of Organic Chemistry 2007, V72(8), P2967-2977.
Safety Data
Hazard Symbols symbol   GHS06 Danger    Details
Hazard Statements H301    Details
Precautionary Statements P264-P270-P301+P316-P321-P330-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H301
SDS Available
up Discovory and Applicatios
4,5,6,7-Tetrafluoro-1H-isoindole-1,3(2H)-dione is a highly fluorinated organic compound that has attracted attention for its unique electronic properties and potential applications in materials science, organic electronics, and medicinal chemistry. The compound belongs to the class of isoindole derivatives, which are known for their rigid structures and aromaticity, as well as their ability to interact with a variety of functional groups. The presence of four fluorine atoms in the molecule significantly alters its chemical and physical properties, including its electronic behavior, solubility, and stability.

The synthesis of 4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione typically involves fluorination reactions, where a precursor isoindole derivative is subjected to halogenation conditions that selectively introduce the fluorine atoms at the 4,5,6, and 7 positions of the aromatic ring. This selective fluorination is often achieved using highly reactive fluorinating agents such as xenon difluoride or Selectfluor under controlled conditions, which allow for the precise incorporation of fluorine into the molecule without disrupting the overall structure. The resulting tetrafluorinated isoindole derivative is then isolated and purified, often as a stable crystalline solid or as a salt for ease of handling.

One of the key applications of 4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione lies in the field of organic electronics. The highly electronegative fluorine atoms significantly enhance the electron-withdrawing properties of the molecule, making it an excellent candidate for use in the development of organic semiconductors and materials for optoelectronic devices. For example, it can be used in the fabrication of organic light-emitting diodes (OLEDs), organic solar cells, and field-effect transistors (OFETs). The fluorinated isoindole derivative, due to its structural rigidity and electronic properties, can also contribute to improved charge transport, stability, and performance of these devices, which are critical for next-generation flexible and lightweight electronic technologies.

In addition to its role in organic electronics, 4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione is also being explored in medicinal chemistry for its potential bioactivity. The fluorine atoms in the molecule play a crucial role in enhancing the compound's pharmacokinetic properties, such as metabolic stability and bioavailability. By modifying the electron density on the aromatic ring, the fluorination can influence the interaction of the compound with biological targets, potentially improving its affinity and specificity. Researchers are investigating its use as a scaffold in the design of novel drug candidates, particularly in the areas of cancer therapy and neurodegenerative diseases, where the compound’s fluorinated structure could impart desirable biological effects.

Moreover, the compound is being studied for its potential as a building block in the synthesis of advanced functional materials. The ability of fluorinated isoindole derivatives to coordinate with metal centers opens up possibilities for their use in catalysis and materials science. For instance, it can be utilized in the development of metal-organic frameworks (MOFs) and other coordination polymers, where the fluorinated isoindole acts as a ligand, providing stability and enhancing the material’s properties. These materials have a wide range of applications in gas storage, sensing, and separations.

In summary, 4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione represents a versatile and highly functional compound with significant potential in a variety of scientific fields. Its discovery and subsequent applications in organic electronics, medicinal chemistry, and material science highlight the importance of fluorine chemistry in advancing modern technologies and addressing challenges in drug development and electronic devices.
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