tert-Butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate
[CAS# 661487-17-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: tert-Butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate
• Synonyms: 5-Boc-3-iodo-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridine
• Molecular Formula: C₁₁H₁₆IN₃O₂
• Molecular Weight: 349.17
• CAS Registry Number: 661487-17-8
• EC Number: 867-000-8
• SMILES: CC(C)(C)OC(=O)N1CCC2=C(C1)C(=NN2)I

Properties

• Solubility: 14.03 mg/L (25 ºC water)
• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.611, Calc.^*
• Melting point: 162.64 ºC
• Boiling Point: 400.74 ºC, 454.4±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 228.6±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

Hazard Classification

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

Discovory and Applicatios

Tert-butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate is a chemical compound of considerable interest in synthetic organic chemistry. Its structure consists of a pyrazolo[4,3-c]pyridine core, which is modified with tert-butyl and iodo functional groups. The unique arrangement of these substituents provides this compound with distinctive chemical properties, making it valuable for various applications.

The discovery of tert-butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate can be attributed to ongoing research aimed at exploring the biological activities of pyrazolo derivatives. Researchers have synthesized various pyrazolo compounds to investigate their potential as pharmacologically active agents. The introduction of iodine in this specific compound not only enhances its reactivity but also allows for subsequent transformations, which are essential in medicinal chemistry.

One of the prominent applications of this compound lies in the field of drug discovery. The pyrazolo[4,3-c]pyridine structure has been recognized for its biological activity, particularly as an antitumor and anti-inflammatory agent. Researchers have identified that substituents on the pyrazolo core can significantly influence biological activity. As such, tert-butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate is being explored for its potential use in developing new therapeutic agents. The iodo group may facilitate the introduction of further functionalization, enabling the optimization of pharmacological properties.

Moreover, this compound has shown promise as a synthetic intermediate in organic synthesis. The presence of the carboxylate group in the structure allows for various coupling reactions, making it a valuable precursor in the synthesis of more complex molecules. This utility in building larger, more complex structures is crucial in chemical research, particularly for synthesizing compounds with desirable properties for pharmaceuticals or agrochemicals.

In addition to its applications in medicinal chemistry, tert-butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate can also be of interest in materials science. The incorporation of halogens, like iodine, into organic frameworks can enhance properties such as solubility, stability, and electronic characteristics. Such properties are critical when developing new materials for electronic applications or polymeric systems.

Despite its potential, research on this compound is still emerging, and comprehensive studies are required to elucidate its full range of biological and chemical properties. Ongoing investigations are expected to provide insights into optimizing the synthesis and expanding the utility of this compound in various fields.

In conclusion, tert-butyl 3-iodo-1H,4H,5H,6H,7H-pyrazolo[4,3-c]pyridine-5-carboxylate represents a significant advancement in the realm of pyrazolo derivatives, particularly for its applications in drug discovery and synthetic chemistry. As research continues to uncover its potential, this compound may play a pivotal role in developing new therapeutic agents and enhancing synthetic methodologies in organic chemistry.