What Is Methyl 5-Bromo-6-Methyl-1H-indazole-3-carboxylate?

Methyl 5-bromo-6-methyl-1H-indazole-3-carboxylate (Aladdin SKU M678839) is a halogenated indazole derivative bearing three key functional handles: an aryl bromide at the 5-position, a methyl substituent at the 6-position, and a methyl ester at the 3-position of the indazole ring system. The indazole core is a bicyclic heteroaromatic scaffold composed of a benzene ring fused to a pyrazole ring, and it appears frequently in bioactive molecules and pharmaceutical candidates. The combination of the electrophilic aryl bromide and the hydrolysable methyl ester makes this compound a particularly flexible intermediate for multistep synthetic sequences in drug discovery and materials research.

Key Chemical Properties and Handling

As a brominated aromatic ester, methyl 5-bromo-6-methyl-1H-indazole-3-carboxylate is a solid at room temperature. The indazole NH proton renders the compound amphoteric in a sense: it can act as a weak acid (NH) or coordinate through the ring nitrogens. The methyl ester is susceptible to hydrolysis under strongly acidic or basic aqueous conditions; therefore, reactions should be performed under conditions compatible with ester stability unless ester hydrolysis to the carboxylic acid is intentional.

For handling, standard laboratory precautions for fine chemical reagents apply. Work in a well-ventilated fume hood, wear appropriate personal protective equipment (gloves, lab coat, eye protection), and avoid inhalation of dust. Consult the Safety Data Sheet (SDS) prior to use for full hazard information specific to this compound.

Storage and Stability

To maintain the integrity of methyl 5-bromo-6-methyl-1H-indazole-3-carboxylate over time, store the compound in a tightly sealed container under cool, dry, and dark conditions. Refrigerated storage (2–8 °C) is generally recommended for halogenated indazole building blocks to minimise degradation. Protect from prolonged exposure to moisture and strong light. When removing material from cold storage, allow the container to equilibrate to room temperature before opening to prevent condensation from contaminating the sample.

Specific confirmed long-term stability data are not included in the current source material; consult Aladdin Scientific's technical team or the SDS for validated shelf-life information.

Synthetic Applications and Cross-Coupling Reactions

The aryl bromide at the 5-position of this indazole is the primary synthetic handle for palladium- or nickel-catalysed cross-coupling reactions. Common transformations include:

• Suzuki–Miyaura coupling: introduction of aryl or heteroaryl boronic acids/esters to build biaryl or heteroaryl-indazole architectures prevalent in kinase inhibitors and other drug classes.
• Buchwald–Hartwig amination: formation of C–N bonds to install amino groups, useful for generating amine-containing pharmacophores.
• Negishi or Kumada coupling: use of organozinc or organomagnesium reagents for carbon–carbon bond formation when alternative nucleophiles are required.

The methyl ester at C-3 provides an additional point of diversification: it can be hydrolysed to the free carboxylic acid, reduced to the alcohol, converted to amides via aminolysis, or used in condensation reactions. The indazole NH can be protected (e.g., with a Boc or SEM group) when N-selective transformations are needed. Together, these features make the compound a highly versatile scaffold in library synthesis and lead optimisation campaigns.

Ordering, Availability, and Quality

Methyl 5-bromo-6-methyl-1H-indazole-3-carboxylate is available from Aladdin Scientific under SKU M678839. The compound is also cross-referenced as Pharmablock catalogue number PBLJ4076, which may assist researchers in locating literature or supplier comparisons. For current pricing, available pack sizes, purity certificates, and stock status, please contact Aladdin Scientific's sales team or visit the product page on the Aladdin website.

Aladdin Scientific provides reagents for research use only. Always verify suitability for your specific application and consult the accompanying analytical data (e.g., HPLC purity, NMR) supplied with each lot.