methyl 1H-indole-3-carboxylate

• ChemBase ID: 7885
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: c1ccc2c(c1)[nH]cc2C(=O)OC
• Canonical SMILES: COC(=O)c1c[nH]c2c1cccc2
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 1H-indole-3-carboxylate
• IUPAC Traditional name: methyl 1H-indole-3-carboxylate
• Synonyms: 3-Methoxycarbonylindole; 3-Carbomethoxyindole; Methyl indolyl-3-carboxylate; Methyl indole-3-carboxylate; methyl 1H-indole-3-carboxylate; Methyl indole-3-carboxylate; Indole-3-carboxylic acid methyl ester; Methyl 3-indolecarboxylate; 吲哚-3-甲酸甲酯

Database IDs

• CAS Number: 942-24-5
• MDL Number: MFCD00189407
• Beilstein Number: 142023
• PubChem SID: 160971192; 24864651
• PubChem CID: 589098

CALCULATED PROPERTIES

• Acid pKa: 12.198919
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.0754848
• LogD (pH = 7.4): 2.075478
• Log P: 2.0754848
• Molar Refractivity: 49.1698 cm^3
• Polarizability: 19.968628 Å^3
• Polar Surface Area: 42.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 149-152 °C(lit.); 149-152°C; 149-152°C

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%; 99%
• Empirical Formula (Hill Notation): C10H9NO2

DETAILS

Sigma Aldrich - 395307

Packaging
25, 100 g in glass bottle
Application
Reactant for preparation of:
• Nitric oxide synthase (nNOS) inhibitorS1
• Protein kinase c alpha (PKCα) inhibitors2
• Inhibitors of the C-terminal domain of RNA polymerase II as antitumor agents
• Kinase insert domain receptor (KDR) inhibitors3
• Organocatalysts for the anti-Mannich reaction4
• Very late antigen-4 (VLA-4) antagonists5
• Inhibitors of Human 5-Lipoxygenase6
• Serotonin 5-HT4 receptor antagonists7
• Hyaluronidase inhibitors8Reactant for:
• Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions†