General Description

N,N'-Bis-Boc-1-guanylpyrazole is a versatile compound with a molecular formula of C14H22N4O4 and molecular weight of 310.35 g/mol. It is known for its reactivity in organic synthesis, functioning as a catalyst in aldol reactions and serving as a precursor for bis(guanylhydrazones) synthesis. This white to off-white crystalline powder exhibits limited water solubility, making it suitable for handling and storage. Its applications in medicinal chemistry and drug discovery are attributed to its ability to introduce guanidine functionalities, enabling the creation of diverse guanidine-containing compounds with potential therapeutic effects. However, cautious handling and adherence to safety measures are crucial due to limited specific safety information.

Figure 1. N,N'-bis-boc-1-guanylpyrazole

Properties

N,N'-bis-boc-1-guanylpyrazole is a chemical compound with a molecular formula of C14H22N4O4 and a molecular weight of 310.35 g/mol. It exists as a white to off-white crystalline powder that has limited solubility in water. This compound finds widespread use as a reagent in organic synthesis due to its versatile reactivity towards various functional groups. One of the notable properties of N,N'-bis-boc-1-guanylpyrazole is its nucleophilicity, which allows it to act as a catalyst in aldol reactions. It facilitates the formation of carbon-carbon bonds by reacting with carbonyl compounds. Additionally, it serves as a precursor for the synthesis of bis(guanylhydrazones), which have applications in medicinal chemistry and coordination chemistry. The presence of the boc (tert-butyloxycarbonyl) protecting group in this compound enhances its stability and allows for selective reactions. The compound's crystalline nature and solid form make it convenient for handling and storage. In summary, N,N'-bis-boc-1-guanylpyrazole exhibits desirable properties such as reactivity towards various functional groups, nucleophilicity for aldol reactions, and suitability as a precursor for bis(guanylhydrazones) synthesis. Its crystalline powder form and limited water solubility further contribute to its usefulness in organic synthesis applications. ¹

Applications

N,N'-Bis-Boc-1-guanylpyrazole is a compound commonly used in organic synthesis for its guanidinylating properties. It plays a significant role in the stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin. The compound finds applications in the field of medicinal chemistry and drug discovery. It can be utilized as a key reagent in the construction of complex organic molecules due to its ability to introduce guanidine functionalities. The guanidine moiety is an important pharmacophore found in various biologically active compounds. By incorporating this group into molecular structures, researchers can explore the potential therapeutic effects and interactions with biological targets. N,N'-Bis-Boc-1-guanylpyrazole has been employed in the synthesis of diverse guanidine-containing compounds such as natural products, peptidomimetics, and enzyme inhibitors. Its precise guanidinylating capability allows for the selective modification of target molecules, enabling the creation of novel chemical entities with desired biological activities. In summary, N,N'-Bis-Boc-1-guanylpyrazole serves as a valuable tool in organic synthesis, particularly in the preparation of guanidine derivatives with potential medicinal applications. ²

Safety

N,N'-Bis-Boc-1-guanylpyrazole is a chemical compound that requires careful handling and precautionary measures to ensure safety. It is important to note that this compound has not been specifically classified under the Globally Harmonized System of Classification and Labelling of Chemicals (GHS). When working with N,N'-Bis-Boc-1-guanylpyrazole, it is recommended to wear appropriate personal protective equipment, including gloves, clothing, and eyewear, to minimize the risk of skin and eye irritation. In case of accidental contact with the compound, promptly rinse the affected area with water for at least 15 minutes. If irritation persists or worsens, seek medical attention immediately. To ensure safe storage, N,N'-Bis-Boc-1-guanylpyrazole should be kept in a cool, dry, and well-ventilated area, away from incompatible materials and potential sources of ignition. It is crucial to follow proper disposal methods to prevent environmental contamination and adhere to local regulations regarding the disposal of hazardous chemicals. Although there may be limited specific information available on the safety of N,N'-Bis-Boc-1-guanylpyrazole, it is essential to prioritize caution and consult relevant safety data sheets or expert advice when handling this compound. ³

Reference

1. National Center for Biotechnology Information (2023). PubChem Compound Summary for CID 4428040, N,N'-Di-Boc-1H-pyrazole-1-carboxamidine.

2. Reid CM, Ebikeme C, Barrett MP, Patzewitz EM, Müller S, Robins DJ, Sutherland A. Synthesis of novel benzamidine- and guanidine-derived polyazamacrocycles: Selective anti-protozoal activity for human African trypanosomiasis. Bioorg Med Chem Lett. 2008 Oct 15;18(20):5399-5401.

3. N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine. European Chemicals Agency, EC / List no. 629-085-8.