5-(benzyloxy)-1H-indole-3-carbaldehyde

• ChemBase ID: 15083
• Molecular Formular: C16H13NO2
• Molecular Mass: 251.27992
• Monoisotopic Mass: 251.09462866
• SMILES: c1(OCc2ccccc2)cc2c(cc1)[nH]cc2C=O
• Canonical SMILES: O=Cc1c[nH]c2c1cc(OCc1ccccc1)cc2
• InChI: InChI=1S/C16H13NO2/c18-10-13-9-17-16-7-6-14(8-15(13)16)19-11-12-4-2-1-3-5-12/h1-10,17H,11H2
• InChIKey: DJGNUBADRQIDNQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(benzyloxy)-1H-indole-3-carbaldehyde
• IUPAC Traditional name: 5-(benzyloxy)-1H-indole-3-carbaldehyde
• Synonyms: 5-Benzyloxyindole-3-carbaldehyde; 5-(Phenylmethoxy)-1H-indole-3-carboxaldehyde; 5-Benzyloxy-3-indolecarboxaldehyde; 5-Benzyloxyindole-3-carboxaldehyde; 5-Benzyloxy-3-formylindole; NSC 71049; 5-Benzyloxyindole-3-carboxaldehyde; 5-(benzyloxy)-1H-indole-3-carbaldehyde; 5-Benzyloxy-3-formyl-1H-indole; 5-(Benzyloxy)-1H-indole-3-carboxaldehyde; 5-苄氧基吲哚-3-甲醛

Database IDs

• CAS Number: 6953-22-6
• EC Number: 230-134-7
• MDL Number: MFCD00014562
• Beilstein Number: 208873
• PubChem SID: 24891532; 160978390
• PubChem CID: 81398

CALCULATED PROPERTIES

• Acid pKa: 13.778289
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.351312
• LogD (pH = 7.4): 3.351312
• Log P: 3.351312
• Molar Refractivity: 74.8043 cm^3
• Polarizability: 29.581509 Å^3
• Polar Surface Area: 42.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol
• Apperance: Yellow Powder; yellow to brown powder
• Melting Point: 236-238°C; 237-238°C; 239-242°C; 239-242°C

Safety Information

• Storage Warning: Air Sensitive; IRRITANT, AIR SENSITIVE; Irritant/Light Sensitive/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02154845

Yellow to brown powder.

Sigma Aldrich - B0751

Application
Reactant for preparation of:
• Rhodanine merocyanine dyes1
• Potential topoisomerase II inhibitors2
• Azithromycin derivatives3
• Inhibitors of PI3 kinase-α and the mammalian target of rapamycin4
• Cytotoxic agents5
• Vascular endothelial growth factor (VEGF) inhibitor6
• Derivatives of vancomycin and eremomycin7
• Benzimidazoles as potential antibacterial agents8
• Light-dependent tumor necrosis factor-α antagonists9
• Serotonin 5-HT4 Receptor agonists10

Toronto Research Chemicals - B285948

An antibacterial agent.

REFERENCES

• Amyes, S., et al.: J. Med. Microbiol., 46, 436 (1997)
• Wright, G., et al.: Chem. Biol., 7, 127, (1997)
• Rybak, M., et al.: Drugs, 61, 1 (1997)
• He, Y; Bioorg. Med. Chem. Lett., 13, 3253 (1997)