tert-Butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate
[CAS# 657428-55-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate
• Molecular Formula: C₁₀H₁₄IN₃O₂
• Molecular Weight: 335.14
• CAS Registry Number: 657428-55-2
• SMILES: CC(C)(C)OC(=O)N1CC2=C(C1)NN=C2I

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.629, Calc.^*
• Boiling Point: 435.0±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 216.9±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

tert-Butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate is a chemical compound belonging to the class of heterocyclic pyrazole derivatives. This substance is notable for its unique structure, which incorporates both a pyrrole ring and a pyrazole ring, two key heterocycles commonly found in biologically active compounds. The presence of an iodine atom at the third position of the pyrrole ring, along with a tert-butyl ester group at the carboxylate position, adds significant reactivity to the compound. The structure enables a variety of chemical reactions, making it a versatile intermediate in organic synthesis.

The discovery of tert-butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate likely arose from efforts to explore novel heterocyclic compounds with potential bioactivity and synthetic utility. Its synthesis can be achieved through multiple methods involving the condensation of various pyrazole and pyrrole precursors. Researchers have shown interest in its structure because of the diverse reactions that can be induced by the iodine atom, which serves as an electrophilic center, facilitating nucleophilic substitution and other reactions.

The primary application of tert-butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate is in the field of medicinal chemistry, where it has been investigated for its potential pharmacological properties. The heterocyclic pyrazole and pyrrole systems are known for their ability to interact with various biological targets, including enzymes and receptors, making them attractive scaffolds for drug development. This particular compound may exhibit promising antimicrobial, anticancer, or anti-inflammatory properties, though further research and clinical testing are needed to validate these potential applications. The iodine atom also contributes to the compound's reactivity, potentially enhancing its ability to bind to specific targets within biological systems.

In addition to its medicinal chemistry applications, tert-butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate is useful as an intermediate in organic synthesis. The iodine atom serves as a leaving group in various substitution reactions, making it an important building block in the synthesis of more complex molecules. This reactivity is valuable in the creation of new materials, including functionalized polymers and specialty chemicals used in the electronics or materials science industries.

Moreover, the compound can be employed in the design of chemical probes for studying biological processes. Researchers in the field of chemical biology often utilize such intermediates to develop selective inhibitors of specific enzymes or pathways. By modifying the functional groups attached to the heterocyclic rings, scientists can tune the properties of the compound to optimize its biological activity, leading to more potent and selective compounds for experimental use.

In conclusion, tert-butyl 3-iodo-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate is a valuable compound in both medicinal chemistry and synthetic organic chemistry. Its unique structure, featuring a pyrrole-pyrazole fusion and reactive iodine center, provides a foundation for various chemical reactions and biological interactions. The ongoing exploration of its pharmacological potential and its utility as a synthetic intermediate suggests that this compound will continue to be of interest to researchers in both academia and industry.