Description

5-Methoxy-2-nitrobenzoic acid (CAS No. 1882-69-5) is a high-purity nitrobenzoic acid derivative with the molecular formula C₈H₇NO₅. This compound is characterized by its methoxy and nitro functional groups positioned at the 5- and 2-positions of the benzoic acid ring, respectively, making it a valuable intermediate in organic synthesis and pharmaceutical research. With a molecular weight of 197.15 g/mol, it is supplied as a fine crystalline powder with exceptional purity (>98%) to ensure reproducibility in sensitive applications. Ideal for researchers in medicinal chemistry, this compound is compatible with a range of coupling reactions, electrophilic substitutions, and serves as a precursor for advanced heterocyclic frameworks. Packaged under inert conditions to prevent degradation, it is suitable for use in high-throughput screening (HTS), drug discovery, and material science applications.

Properties

• CAS Number: 1882-69-5
• Complexity: 236
• IUPAC Name: 5-methoxy-2-nitro-benzoic acid
• InChI: InChI=1S/C8H7NO5/c1-14-5-2-3-7(9(12)13)6(4-5)8(10)11/h2-4H,1H3,(H,10,11)
• InChI Key: URADKXVAIGMTEG-UHFFFAOYSA-N
• Exact Mass: 197.03242232
• Molecular Formula: C8H7NO5
• Molecular Weight: 197.14
• SMILES: COC1=CC(=C(C=C1)[N+](=O)[O-])C(=O)O
• Topological: 92.4
• Monoisotopic Mass: 197.03242232
• Synonyms: 5-Methoxy-2-nitrobenzoic acid, 1882-69-5, DTXSID90320805, DTXCID10271926, 606-135-7, Benzoic acid, 5-methoxy-2-nitro-, 2-Nitro-5-methoxybenzoic acid, MFCD00151836, 5-methoxy-2-nitro-benzoic acid, 5-methoxy-nitrobenzoic acid, 6-Nitro-m-anisic Acid, 5-Methoxy-2-nitrobenzoicAcid, NSC364656, SCHEMBL269614, 2-nitro-5-methoxy benzoic acid, 5-(methyloxy)-2-nitrobenzoic acid, BCP28909, STR05879, SBB028524, 5-Methoxy-2-nitrobenzoic acid, 97%, AKOS000147444, AC-1099, CS-W002435, FM64217, NSC 364656, NSC-364656, SY002263, DB-044670, A8146, M2245, NS00125762, ST50405872, EN300-51143, 6-Nitro-m-anisic Acid;2-Nitro-5-methoxybenzoic acid, Z90146674, F0001-0675, InChI=1/C8H7NO5/c1-14-5-2-3-7(9(12)13)6(4-5)8(10)11/h2-4H,1H3,(H,10,11

Application

5-Methoxy-2-nitrobenzoic acid is widely utilized as a key synthetic intermediate in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its reactive nitro and carboxyl groups enable facile derivatization, making it valuable for constructing complex molecules such as benzodiazepines and nonsteroidal anti-inflammatory drugs (NSAIDs). Researchers also employ it in the development of fluorescent probes and photoactive materials due to its electron-withdrawing properties. Additionally, it serves as a model substrate in studies of enzymatic decarboxylation and nitration mechanisms.

Safety and Hazards

GHS Hazard Statements

• H302 (12.5%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (87.5%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (87.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (12.5%)
• Skin Irrit. 2 (87.5%)
• Eye Irrit. 2 (87.5%)
• STOT SE 3 (75%)

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