4-(benzyloxy)-1H-indole

• ChemBase ID: 11796
• Molecular Formular: C15H13NO
• Molecular Mass: 223.26982
• Monoisotopic Mass: 223.09971404
• SMILES: [nH]1ccc2c(cccc12)OCc1ccccc1
• Canonical SMILES: c1ccc(cc1)COc1cccc2c1cc[nH]2
• InChI: InChI=1S/C15H13NO/c1-2-5-12(6-3-1)11-17-15-8-4-7-14-13(15)9-10-16-14/h1-10,16H,11H2
• InChIKey: LJFVSIDBFJPKLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(benzyloxy)-1H-indole
• IUPAC Traditional name: 4-(benzyloxy)-1H-indole
• Synonyms: 4-(benzyloxy)-1H-indole; NSC 92539; 4-Benzyloxyindole; 4-Benzyloxyindole; 4-(Benzyloxy)-indole; 4-(Phenylmethoxy)-1H-indole; 4-Benzyloxy-1H-indole; 4-苄氧基吲哚; 4-苯甲氧基吲哚

Database IDs

• CAS Number: 20289-26-3
• EC Number: 243-690-0
• MDL Number: MFCD00047200
• Beilstein Number: 183150
• PubChem SID: 24854794; 160975103
• PubChem CID: 88465

CALCULATED PROPERTIES

• Acid pKa: 16.638346
• 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: 27.744276 Å^3
• Polar Surface Area: 25.02 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Ethyl Acetate
• Apperance: Off-White Crystalline Solid with Few Darker
• Melting Point: 57-61 °C(lit.); 57-61°C; 58-60°C; 59-61°C; 59-61°C

Safety Information

• Storage Warning: IRRITANT; Irritant/Light Sensitive/Store under Argon/Keep Cold
• 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: 98%; 99%
• Empirical Formula (Hill Notation): C15H13NO

DETAILS

Sigma Aldrich - 246212

Packaging
1 g in glass bottle
Application

• Reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition1
• Reactant for preparation of indoles by Bartoli reductive cyclization as useful intermediates in medicinal chemistry research2
• Reactant for synthesis of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer3
• Reactant for preparation of HCV inhibitors4
• Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands5
• Reactant for preparation of 4-aryl-4H-chromenes as apoptosis inducers6

Toronto Research Chemicals - B285944

Indole derivative as substrate-binding; N297Q and I300V mutants of cytochrome P 450 2A6 display expansion of substrate specificity of cytochrome P 450 2A6 to oxidize substituted indoles.

REFERENCES

• Gotoh, O., et al.: J. Biol. Chem., 267, 83 (1992)
• Guengerich, F., et al.: Chem. Res. Toxicol., 14, 611 (1992)
• Kim, D., et al.: Biochemistry, 43, 981 (1992)