For researchers and industrial chemists, a deep understanding of chemical synthesis and properties is fundamental to successful product development. 5-Carboxyoxindole, identified by its CAS number 102359-00-2, is a fascinating organic molecule whose synthesis and inherent properties make it a valuable intermediate in various sophisticated applications, particularly in pharmaceuticals and electronic chemicals.

The synthesis of 2-oxoindoline-5-carboxylic acid, commonly known as 5-Carboxyoxindole, often involves multi-step organic reactions. While specific patented routes may vary, a general approach described in chemical literature involves reactions starting from indole derivatives. For instance, a common pathway might utilize precursors such as 5-chloroacetylindone or related indole acids. The process typically involves reactions like Friedel-Crafts acylation, followed by oxidation or other functional group transformations to introduce the carboxylic acid moiety at the 5-position of the oxindole ring. The precise control of reaction conditions, including temperature, catalysts (like aluminum chloride), and reaction times, is crucial for achieving high yields and the desired purity, often targeting the 97% mark for demanding applications.

From a properties perspective, 5-Carboxyoxindole is typically encountered as an off-white to light orange solid. Its molecular formula is C9H7NO3, and its molecular weight is approximately 177.16 g/mol. Key physical properties, such as its melting point, are generally in the range of 310-316°C, indicating a stable solid at room temperature. Solubility data suggests it has limited solubility in common organic solvents like methanol and DMSO, which can influence its handling and reactivity in different reaction media.

The chemical reactivity of 5-Carboxyoxindole stems from its functional groups: the carboxylic acid (-COOH) and the oxindole core. The carboxylic acid group readily participates in esterification, amidation, and salt formation reactions, making it an excellent handle for further molecular elongation or conjugation. The oxindole moiety itself can undergo various electrophilic aromatic substitution reactions or modifications at the nitrogen atom, offering a broad spectrum of derivatization possibilities.

These characteristics make 5-Carboxyoxindole a sought-after intermediate. In pharmaceutical synthesis, its structure allows for the creation of complex heterocyclic compounds that are common in many drug classes. In the realm of electronic chemicals, its incorporation into photoresist formulations can influence the photochemical behavior and etch resistance, crucial for high-resolution lithography. For R&D scientists and procurement specialists, understanding these synthetic pathways and properties is vital when considering its use in new product development or when sourcing from manufacturers. Engaging with a reputable supplier ensures access to well-characterized material, facilitating predictable outcomes in your chemical endeavors.