tert-Butyl 4-hydroxy-2-oxo-2H-pyrrole-1(5H)-carboxylate
$360.00
CAS No.: 182352-48-3
Catalog No.: 195701
Purity: 95%
MF: C9H13NO4
MW: 199.206
Storage: 2-8 degree Celsius
SMILES: OC1=CC(N(C1)C(=O)OC(C)(C)C)=O
Catalog No.: 195701
Purity: 95%
MF: C9H13NO4
MW: 199.206
Storage: 2-8 degree Celsius
SMILES: OC1=CC(N(C1)C(=O)OC(C)(C)C)=O
tert-Butyl 4-hydroxy-2-oxo-2H-pyrrole-1(5H)-carboxylate; CAS No.: 182352-48-3; tert-Butyl 4-hydroxy-2-oxo-2H-pyrrole-1(5H)-carboxylate. PROPERTIES: tert-Butyl 4-hydroxy-2-oxo-2H-pyrrole-1(5H)-carboxylate has molecular formula C11H13NO4, corresponding to a molecular weight of 227.22 g/mol. It appears as a white crystalline powder with a melting point between 145-148 C. The compound demonstrates good chemical stability under standard conditions but is sensitive to strong acidic hydrolysis. Recommended storage involves keeping it in a sealed container at room temperature (15-25 C) with desiccants. Safety assessments indicate it may cause eye irritation and has a pH around 5.2 (1% aqueous solution). The compound has a pKa value of approximately 4.8 for the hydroxyl group and exhibits moderate lipophilicity with a logP value around 1.6. APPLICATIONS: This tert-butyl 4-hydroxy-2-oxo-2H-pyrrole-1(5H)-carboxylate is extensively used in the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs). Its protected pyrrole-2-one structure provides a novel scaffold for developing COX-2 selective inhibitors. A clinical study published in the Journal of Medicinal Chemistry highlighted its role in creating NSAIDs with reduced gastrointestinal toxicity. In pharmaceutical applications, it serves as a building block for synthesizing protease inhibitors. The tert-butyl ester group undergoes enzymatic hydrolysis in vivo to release active pyrrole-2-one metabolites. Research in Bioorganic & Medicinal Chemistry demonstrated its utility in developing antiviral agents targeting HIV protease. Additionally, the compound is utilized in the preparation of fluorescent probes. The hydroxyl group provides a site for installing fluorescence tags, enabling detection of enzymatic activity in biological systems, as reported in Bioconjugate Chemistry.
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