The precise understanding of a chemical compound's molecular architecture is foundational for its effective utilization in synthesis and research. 1-Boc-4-aminoindazole (CAS 801315-74-2) is a compound whose structural nuances dictate its reactivity and applications, particularly within the realms of organic synthesis and pharmaceutical chemistry. This article delves into the structural components of 1-Boc-4-aminoindazole, explaining how its functional groups contribute to its utility.

Decoding the Molecular Formula: C12H15N3O2

The molecular formula C12H15N3O2 provides a blueprint for the elemental composition of 1-Boc-4-aminoindazole. It indicates the presence of twelve carbon atoms, fifteen hydrogen atoms, three nitrogen atoms, and two oxygen atoms. This composition translates into a molecular weight of approximately 233.27 g/mol, a key parameter for stoichiometric calculations in chemical reactions.

The Indazole Core: A Privileged Heterocycle

At the heart of the molecule lies the indazole ring system. Indazole is a bicyclic aromatic heterocycle composed of a benzene ring fused to a pyrazole ring. This fused system is considered a 'privileged structure' in medicinal chemistry due to its frequent occurrence in biologically active compounds and its ability to engage in diverse interactions with biological targets. The nitrogen atoms within the pyrazole ring contribute to the molecule's electronic properties and potential hydrogen bonding capabilities.

Key Functional Groups: Amino and Boc Protection

Attached to the indazole core at the 4-position is an amino group (-NH2). This primary amine is a nucleophilic and basic functional group, offering a reactive site for a multitude of chemical transformations, such as acylation, alkylation, reductive amination, and formation of amide or urea linkages. These reactions are pivotal for elaborating the molecular structure and building more complex compounds.

Crucially, the nitrogen atom at the 1-position of the indazole ring is protected by a tert-butoxycarbonyl (Boc) group. The Boc group is one of the most widely used protecting groups for amines and nitrogen heterocycles in organic synthesis. It is introduced to selectively block the reactivity of the N-H bond, preventing unwanted side reactions at this position during synthesis. The Boc group is typically stable under basic and mildly acidic conditions but can be readily cleaved under moderately strong acidic conditions (e.g., using trifluoroacetic acid or HCl in organic solvents), regenerating the free N-H functionality when needed. This selective protection and deprotection strategy is fundamental for controlled synthesis.

Implications for Synthesis and Procurement

The strategic placement of these functional groups makes 1-Boc-4-aminoindazole a versatile synthon. Chemists looking to buy 1-Boc-4-aminoindazole leverage its structure for building complex heterocyclic frameworks essential for pharmaceutical intermediates. The predictable reactivity of the amino group and the easily removable Boc protecting group allow for stepwise construction of target molecules. When procuring this compound, understanding its structure reinforces the need for high purity, as impurities could interfere with these precise synthetic steps.

In essence, the structure of 1-Boc-4-aminoindazole is a testament to thoughtful synthetic design, providing a reactive amino group on a biologically relevant indazole scaffold, all while ensuring controlled reactivity through effective Boc protection. This makes it an invaluable tool for chemists in drug discovery and materials science.