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Indole-2-carboxylic acid
Indole-2-carboxylic acid (CAS 1477-50-5) is a strategically functionalized nitrogen heterocyclic scaffold engineered for kinase inhibitor development and CNS drug discovery. Distinct from the more common indole-3-carboxylic acid isomer, this molecule features a carboxylic acid substituent at the C2 position of the indole core, creating a unique electronic distribution and hydrogen-bonding geometry. The C2-carboxylate motif serves as a versatile handle for amide coupling, esterification, or decarboxylative cross-coupling, while the indole nitrogen (N1) offers additional derivatization potential via alkylation or acylation. This intermediate is particularly valuable for constructing ATP-mimetic kinase inhibitors, serotonin receptor modulators, and agrochemical actives where the 2-substituted indole architecture provides distinct binding orientation compared to 3-substituted analogs. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to positionally defined indole architectures with tunable physicochemical properties.
Property
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Product Name
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Indole-2-carboxylic acid
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CAS Number
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1477-50-5
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Chinese Name
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吲哚 -2-羧酸
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Synonyms
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1H-Indole-2-carboxylic acid; 2-Carboxyindole; C₉H₇NO₂ heterocycle; Indole-2-carboxylate
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Chinese Synonyms
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1H-吲哚 -2-羧酸; 2-羧基吲哚; 吲哚 -2-甲酸; 2-位羧酸吲哚
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Molecular Formula
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C₉H₇NO₂
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Molecular Weight
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161.16 g/mol
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Purity
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≥ 98% (HPLC area normalization)
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Product Category
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Pharmaceutical Intermediates / Indole Derivatives / Heterocyclic Carboxylic Acids
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Appearance
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White to Off-white Crystalline Powder
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Melting Point
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202 – 209 °C
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Storage Conditions
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Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed. Protect from strong oxidizing agents and bases to avoid decarboxylation or ring oxidation.
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Shelf Life
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24 months under recommended storage conditions
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Packaging
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100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
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Applications
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Kinase inhibitor synthesis (ATP-mimetic scaffolds), CNS drug scaffold development, serotonin receptor modulator research, amide coupling for peptide mimetics, decarboxylative cross-coupling strategies
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Reactivity
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Suitable for amide coupling (activation via EDC/HATU), esterification, N1-alkylation/acylation, decarboxylative coupling, and electrophilic aromatic substitution at C3/C5
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Special Note
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✅ C2-Substituted Indole—distinct binding orientation vs. C3-isomers (CAS 771-50-6). Carboxylic acid enables direct coupling without hydrolysis step. Part of our indole building block series.
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