Methyl 2-hydroxy-5-nitrobenzoate, also identified by its common synonym Methyl 5-nitrosalicylate, is an important organic compound with the CAS number 17302-46-4. Its molecular formula is C8H7NO5, and it possesses a molecular weight of approximately 197.14 g/mol. This compound is a derivative of salicylic acid, featuring a methyl ester group and a nitro substituent on the aromatic ring. Understanding its chemical properties and common synthesis pathways is crucial for chemists involved in organic synthesis, pharmaceutical research, and agrochemical development.

The structure of Methyl 2-hydroxy-5-nitrobenzoate is characterized by a benzene ring with three key functional groups: a hydroxyl group (-OH) at the 2-position, a nitro group (-NO2) at the 5-position, and a methyl ester (-COOCH3) attached to the carboxyl group. The presence of the electron-withdrawing nitro group and the electron-donating hydroxyl group influences the reactivity of the aromatic ring and the acidity of the phenolic proton. The compound typically appears as a crystalline solid, with reported melting points generally falling in the range of 114-117°C. Its solubility is typically good in common organic solvents, such as ethanol, methanol, and DMSO, while it exhibits limited solubility in water.

Several synthetic routes are employed to prepare Methyl 2-hydroxy-5-nitrobenzoate, often starting from more readily available precursors. One common method involves the esterification of 5-nitrosalicylic acid. 5-Nitrosalicylic acid itself can be synthesized through the nitration of salicylic acid. The direct nitration of salicylic acid, typically using a mixture of concentrated nitric acid and sulfuric acid, preferentially occurs at the 5-position due to the activating and ortho, para-directing nature of the hydroxyl group, though careful control of reaction conditions is necessary to minimize by-product formation and ensure regioselectivity. Once 5-nitrosalicylic acid is obtained, it can be esterified with methanol, often under acidic catalysis (e.g., using sulfuric acid or thionyl chloride), to yield Methyl 2-hydroxy-5-nitrobenzoate.

Another potential synthetic approach might involve starting from methyl salicylate and then performing nitration. However, the directing effects of the hydroxyl and ester groups need careful consideration for regiocontrol. Alternative methods may also exist, such as those involving functional group interconversions on pre-substituted aromatic rings.

The compound's physical and chemical properties make it a valuable intermediate in various chemical transformations. The hydroxyl group can undergo reactions such as etherification or acylation, while the nitro group can be reduced to an amino group, opening pathways to a wide array of amine derivatives. These derivative compounds are often explored for their biological activities, finding use in the development of pharmaceuticals and agrochemicals.

For researchers and chemical manufacturers, understanding these synthesis routes and the compound’s properties is vital for efficient production and application. Sourcing high-purity Methyl 2-hydroxy-5-nitrobenzoate from reliable suppliers is critical for achieving consistent results in downstream reactions. Manufacturers often provide detailed specifications including purity (typically >98%), melting point range, and other relevant analytical data, ensuring that chemists can confidently integrate this intermediate into their synthetic strategies.