2-(1H-indol-3-yl)-2-oxoacetic acid

• ChemBase ID: 58768
• Molecular Formular: C10H7NO3
• Molecular Mass: 189.16748
• Monoisotopic Mass: 189.04259309
• SMILES: c1c2c(ccc1)[nH]cc2C(=O)C(=O)O
• Canonical SMILES: OC(=O)C(=O)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C10H7NO3/c12-9(10(13)14)7-5-11-8-4-2-1-3-6(7)8/h1-5,11H,(H,13,14)
• InChIKey: DWLVFWDCSFTDOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1H-indol-3-yl)-2-oxoacetic acid
• IUPAC Traditional name: 1H-indol-3-yl(oxo)acetic acid
• Synonyms: 1H-Indol-3-yl(oxo)acetic acid; NSC 71954; 3-Indoleglyoxylic acid; 3-吲哚乙醛酸

Database IDs

• CAS Number: 1477-49-2
• EC Number: 216-029-9
• MDL Number: MFCD00005625
• PubChem SID: 162063531; 24853160
• PubChem CID: 73863

CALCULATED PROPERTIES

• Acid pKa: 3.1506383
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7343329
• LogD (pH = 7.4): -1.8644902
• Log P: 1.5892495
• Molar Refractivity: 49.3422 cm^3
• Polarizability: 19.779108 Å^3
• Polar Surface Area: 70.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 217 °C (dec.)(lit.)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C10H7NO3

DETAILS

Sigma Aldrich - 220019

Packaging
1, 5 g in glass bottle
Application

• Reactant for synthesis of fenbufen and ethacrynic acid derivatives1
• Reactant for preparation of glyoxyl analogs of indole phytoalexins as anticancer agents2
• Reactant for synthesis of tertiary amides3
• Reactant for preparation of fuconojirimycin derivatives as inhibitors of α-Fucosidases4
• Reactant for total synthesis of oxazinin-3 from 3-indoleglyoxylic acid via an intramolecular addition/cyclization reactions5