395307

Methylindol-3-carboxylat

99%

• Synonym(e): 3-Carbomethoxyindole, 3-Methoxycarbonylindole, Methyl indolyl-3-carboxylate
• Empirische Formel (Hill-System): C₁₀H₉NO₂
• CAS-Nummer: 942-24-5
• Molekulargewicht: 175.18
• MDL-Nummer: MFCD00189407
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24864651
• NACRES: NA.22

Eigenschaften

• Assay: 99%
• Form: powder
• mp (Schmelzpunkt): 149-152 °C (lit.)
• SMILES String: COC(=O)c1c[nH]c2ccccc12
• InChI: 1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3
• InChIKey: QXAUTQFAWKKNLM-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Methyl indole-3-carboxylate (3-Methoxycarbonylindole, 3-Carbomethoxyindole, Methyl indolyl-3-carboxylate) has been extracted from the marine Streptomyces sp. 060524. Its crystal structure indicates the presence of inter­molecular N-H…O hydrogen bond. It is also obtained during the isolation of sorazinones A and B from Sorangium cellulosum strain Soce895. It undergoes regioselective dibromination with bromine in acetic acid to afford methyl 5,6-dibromoindole-3-carboxylate.

Anwendung

Reactant for preparation of:

• Nitric oxide synthase (nNOS) inhibitorS
• Protein kinase c alpha (PKCα) inhibitors
• Inhibitors of the C-terminal domain of RNA polymerase II as antitumor agents
• Kinase insert domain receptor (KDR) inhibitors
• Organocatalysts for the anti-Mannich reaction
• Very late antigen-4 (VLA-4) antagonists
• Inhibitors of Human 5-Lipoxygenase
• Serotonin 5-HT4 receptor antagonists
• Hyaluronidase inhibitors

Reactant for:

• Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions†

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves