1-(3-hydroxy-1H-indol-1-yl)ethan-1-one

• ChemBase ID: 159312
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: c1ccc2c(c1)c(cn2C(=O)C)O
• Canonical SMILES: Oc1cn(c2c1cccc2)C(=O)C
• InChI: InChI=1S/C10H9NO2/c1-7(12)11-6-10(13)8-4-2-3-5-9(8)11/h2-6,13H,1H3
• InChIKey: NNJXIAOPPYUVAX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-hydroxy-1H-indol-1-yl)ethan-1-one
• IUPAC Traditional name: acetylindoxyl
• Synonyms: N-Acetyl-3-indolol; 1-(3-Hydroxyindol-1-yl)ethanone; N-Acetyl-3-hydroxyindole

Database IDs

• CAS Number: 16800-68-3; 33025-60-4
• PubChem SID: 162253447
• PubChem CID: 439701

CALCULATED PROPERTIES

• Acid pKa: 8.090309
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0871587
• LogD (pH = 7.4): 1.0092955
• Log P: 1.0882516
• Molar Refractivity: 48.3957 cm^3
• Polarizability: 19.88224 Å^3
• Polar Surface Area: 42.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 134-136°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - A178950

A useful synthetic intermediate. Auxin like molecule, used in the preparation of peptidomimetics.

REFERENCES

• Jochmans, D., et al.: J. Virol., 80, 12283 (2006)
• Zhang, W., et al.: Bioorg. Med. Chem., 17, 2077 (2006)