Iodobenzene diacetate
[CAS# 3240-34-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: Iodobenzene diacetate
• Synonyms: (Diacetoxyiodo)benzene; Iodosobenzene diacetate; PIA
• Molecular Formula: C₁₀H₁₁IO₄
• Molecular Weight: 322.10
• CAS Registry Number: 3240-34-4
• EC Number: 221-808-1
• SMILES: CC(=O)OI(C1=CC=CC=C1)OC(=O)C

Properties

• Melting point: 161-165 °C
• Water solubility: INSOLUBLE

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Iodobenzene diacetate is a versatile chemical compound with significant applications in organic synthesis and medicinal chemistry. This compound is derived from iodobenzene, where the iodine atom is replaced by an acetate group at two positions on the benzene ring. Its chemical formula is C8H7IO2, and it is known for its reactivity and utility in various chemical transformations.

The discovery of iodobenzene diacetate can be traced back to advancements in halogenated organic compounds and their applications in synthetic chemistry. Researchers have long sought effective methods for introducing functional groups into aromatic rings, and iodobenzene diacetate emerged as a useful reagent for these purposes. Its development was driven by the need for a reagent that could facilitate the introduction of acyl groups into aromatic systems while maintaining high selectivity and reactivity.

One of the primary applications of iodobenzene diacetate is in the field of organic synthesis, particularly in the formation of various functionalized aromatic compounds. It serves as an electrophilic reagent in the oxidative coupling reactions and can participate in a range of reactions to introduce acyl groups into aromatic systems. For instance, iodobenzene diacetate can be used in the synthesis of substituted aromatic compounds through the introduction of acetyl groups. This process is valuable for creating diverse molecular structures with potential applications in pharmaceuticals and materials science.

In addition to its use in synthetic organic chemistry, iodobenzene diacetate finds applications in medicinal chemistry. Its reactivity makes it a suitable candidate for developing novel pharmaceutical agents and for modifying existing drug structures. By introducing acetyl groups into specific positions on aromatic rings, researchers can alter the biological activity and pharmacokinetics of drug molecules. This capability is particularly useful in drug development, where fine-tuning the properties of compounds is crucial for optimizing their efficacy and safety profiles.

Furthermore, iodobenzene diacetate plays a role in the development of chemical probes and tools for studying biological systems. Its ability to form covalent bonds with target molecules allows for the creation of selective probes that can be used in biochemical assays and imaging techniques. These probes are valuable for understanding the interactions between molecules and for identifying potential drug targets.

The use of iodobenzene diacetate also extends to the synthesis of complex organic molecules and the development of new chemical methodologies. Its versatility as a reagent enables the construction of intricate molecular frameworks and the exploration of novel reaction pathways. This contributes to the advancement of chemical research and the discovery of new compounds with potential applications in various fields.

Overall, iodobenzene diacetate represents a significant advancement in the field of organic chemistry. Its discovery and applications underscore its importance as a reagent and tool for synthetic and medicinal chemistry. The compound's ability to facilitate the introduction of functional groups into aromatic systems and its utility in drug development and chemical research highlight its valuable contributions to the advancement of chemical sciences.

References

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2024. Reactivity and philicity of phthalimide-N-oxyl and benzotriazol-N-oxyl radicals in addition reactions to vinyl compounds. Reaction Kinetics, Mechanisms and Catalysis, 2024, 113(4), 637-647.
DOI: 10.1007/s11144-024-02738-3

2024. Hexafluoroisopropanol-assisted selective intramolecular synthesis of heterocycles by single-electron transfer. Nature Synthesis, 2024, 3(5), 340-347.
DOI: 10.1038/s44160-024-00566-w