6-(benzyloxy)-1H-indole

• ChemBase ID: 13780
• Molecular Formular: C15H13NO
• Molecular Mass: 223.26982
• Monoisotopic Mass: 223.09971404
• SMILES: [nH]1ccc2ccc(cc12)OCc1ccccc1
• Canonical SMILES: c1ccc(cc1)COc1ccc2c(c1)[nH]cc2
• InChI: InChI=1S/C15H13NO/c1-2-4-12(5-3-1)11-17-14-7-6-13-8-9-16-15(13)10-14/h1-10,16H,11H2
• InChIKey: FPMICYBCFBLGOZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(benzyloxy)-1H-indole
• IUPAC Traditional name: 6-(benzyloxy)-1H-indole
• Synonyms: 6-(Phenylmethoxy)-1H-indole; 6-(Benzyloxy)-indole; 6-(Benzyloxy)-1H-indole; NSC 92538; 6-Benzyloxyindole; 6-(Benzyloxy)-1H-indole 98%; 6-Benzyloxyindole; 6-(benzyloxy)-1H-indole; 6-苄氧基吲哚

Database IDs

• CAS Number: 15903-94-3
• EC Number: 000-000-0
• MDL Number: MFCD00053554
• Beilstein Number: 173319
• PubChem SID: 160977087; 24891808
• PubChem CID: 260804

CALCULATED PROPERTIES

• Acid pKa: 16.338194
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.6388097
• LogD (pH = 7.4): 3.6388097
• Log P: 3.6388097
• Molar Refractivity: 68.2203 cm^3
• Polarizability: 27.739756 Å^3
• Polar Surface Area: 25.02 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Diethyl Ether; Ethanol; Ethyl Acetate; Methanol
• Apperance: Colourless Crystalline Solid; yellow to brown crystalline
• Melting Point: 114-116°C; 114-116°C; 118-121°C

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant/Keep Cold
• German water hazard class: 3
• TSCA Listed: false; 否
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%

DETAILS

MP Biomedicals - 02154843

Yellow to brown crystals.

Sigma Aldrich - B5131

Application

• Reactant for enantioselective synthesis of quaternary carbon-containing 3-(3-indolyl)isoindolin-1-ones1
• Reactant for Friedel-Crafts alkylation reactions with hydroxyisoindolinones2
• Reactant for direct and regioselective synthesis of β-heteroarylated ketones3
• Reactant for preparation of hepatitis C virus (HCV) inhibitors4
• Reactant for preparation of protein kinase C (PKC) inhibitors5
• Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands6

Toronto Research Chemicals - B285945

Indole derivative, as antiviral and antitumor agent.

REFERENCES

• Borza, I., et al.: J. Med. Chem., 50, 901 (2007)
• Lefoix, M., et al.: Bioorg. Med. Chem., 16, 5303 (2007)
• Frost, J., et al.: J. Med. Chem., 51, 1904 (2007)