2-[5-(benzyloxy)-1H-indol-3-yl]acetonitrile

• ChemBase ID: 76940
• Molecular Formular: C17H14N2O
• Molecular Mass: 262.30586
• Monoisotopic Mass: 262.11061308
• SMILES: [nH]1c2c(cc(cc2)OCc2ccccc2)c(c1)CC#N
• Canonical SMILES: N#CCc1c[nH]c2c1cc(OCc1ccccc1)cc2
• InChI: InChI=1S/C17H14N2O/c18-9-8-14-11-19-17-7-6-15(10-16(14)17)20-12-13-4-2-1-3-5-13/h1-7,10-11,19H,8,12H2
• InChIKey: ADPRFNVFBYHCJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[5-(benzyloxy)-1H-indol-3-yl]acetonitrile
• IUPAC Traditional name: 2-[5-(benzyloxy)-1H-indol-3-yl]acetonitrile
• Synonyms: 5-(Benzyloxy)-3-(cyanomethyl)-1H-indole; [5-(Benzyloxy)-1H-indol-3-yl]acetonitrile; 5-Benzyloxyindole-3-acetonitrile; NSC 73391; (5-Benzyloxyindol-3-yl)acetonitrile; 5-BENZYLOXYINDOLE-3-ACETONITRILE; 5-苄氧基吲哚-3-乙腈

Database IDs

• CAS Number: 2436-15-9
• MDL Number: MFCD00022730
• PubChem SID: 162041839; 24880386
• PubChem CID: 252139

CALCULATED PROPERTIES

• Acid pKa: 14.351334
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3345068
• LogD (pH = 7.4): 3.3345068
• Log P: 3.3345068
• Molar Refractivity: 78.5072 cm^3
• Polarizability: 31.215479 Å^3
• Polar Surface Area: 48.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-80 °C(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C17H14N2O

DETAILS

MP Biomedicals - 05213700

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 567701

Packaging
5 g in glass bottle
Application

• Reactant for preparation of of β-carboline derivatives as antioxidants in the LDL oxidation model1
• Reactant for preparation of indole-N-acetic acid derivatives as aldose reductase inhibitors for diabetic complications treatment2
• Reactant for preparation of tryptamine analogs as antihypertensive agents3