methyl 2-(1H-indol-3-yl)-2-oxoacetate

• ChemBase ID: 58769
• Molecular Formular: C11H9NO3
• Molecular Mass: 203.19406
• Monoisotopic Mass: 203.05824315
• SMILES: c1c2c(ccc1)[nH]cc2C(=O)C(=O)OC
• Canonical SMILES: COC(=O)C(=O)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C11H9NO3/c1-15-11(14)10(13)8-6-12-9-5-3-2-4-7(8)9/h2-6,12H,1H3
• InChIKey: VFIJGAWYVXDYLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(1H-indol-3-yl)-2-oxoacetate
• IUPAC Traditional name: methyl 2-(1H-indol-3-yl)-2-oxoacetate
• Synonyms: Methyl 2-(indol-3-yl)-2-oxoacetate; Methyl 3-indoleglyoxylate; INDOLE-3-GLYOXYLIC METHYLESTER; Methyl 1H-indol-3-yl(oxo)acetate; Methyl 2-(1H-indol-3-yl)-2-oxoacetate; Methyl (Indol-3-yl)oxoacetate; α-Oxo-1H-indole-3-acetic Acid Methyl Ester; Methyl Indolyl-3-glyoxylate; 吲哚-3-乙醛酸甲酯

Database IDs

• CAS Number: 18372-22-0
• MDL Number: MFCD00047173
• PubChem SID: 24873805; 162063532
• PubChem CID: 588944

CALCULATED PROPERTIES

• Acid pKa: 11.993123
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.9684768
• LogD (pH = 7.4): 1.9684662
• Log P: 1.9684769
• Molar Refractivity: 54.1113 cm^3
• Polarizability: 21.872551 Å^3
• Polar Surface Area: 59.16 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Pale Yellow Fine Powder
• Melting Point: 223-225°C; 227-230 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Temperature Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• 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: 95+%; 98%
• Empirical Formula (Hill Notation): C11H9NO3

DETAILS

MP Biomedicals - 05220791

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 515213

Packaging
5 g in glass bottle
Application

• Reactant for preparation of sotrastaurin analogs as protein kinase inhibitors1
• Reactant for synthesis of GSK-3 inhibitors2
• Reactant for Diels-Alder cycloaddition3
• Reactant for preparation of a Janus kinase 3 inhibitor4
• Reactant for synthesis of cephalandole alkaloids5
• Reactant for stereoselective preparation of COX-2 inhibitor as anticancer agent6
• Reactant for synthesis of cycloalkene indole carbazole alkaloids via ring-closing metathesis7