1H-indol-3-yl(naphthalen-1-yl)methanone

Properties of 1H-Indol-3-yl(naphthalen-1-yl)methanone

1H-Indol-3-yl(naphthalen-1-yl)methanone (also known as 1-(1H-Indol-3-yl)-1-naphthalenylmethanone) is an organic compound belonging to the class of aryl ketones with a fused indole and naphthalene structure. Its molecular formula is C₁₉H₁₃NO, and it has potential applications in medicinal chemistry and material science due to its unique structural features.

Physical Properties:

• Molecular Weight: 271.31 g/mol

• Appearance: Likely a yellow to light brown crystalline solid (exact color may vary based on purity).

• Melting Point: Estimated ~150–200 °C (exact value depends on polymorphic form).

• Solubility:

  • Soluble in organic solvents (DMSO, DMF, chloroform, dichloromethane).

  • Poorly soluble in water due to its aromatic hydrophobic structure.

• Boiling Point: Not well-documented (likely decomposes upon strong heating).

• Spectroscopic Data:

  • IR Spectrum: Expected strong C=O stretch (~1650–1700 cm⁻¹).

  • NMR (¹H & ¹³C): Aromatic protons (δ ~7–9 ppm), indolic NH (~δ 10–12 ppm).

Chemical Properties:

• Reactivity:

  • The carbonyl group (C=O) is electrophilic and may undergo nucleophilic addition or reduction (e.g., to form alcohols).

  • The indole NH can participate in hydrogen bonding or deprotonation under basic conditions.

  • May undergo electrophilic aromatic substitution (EAS) on the naphthalene or indole rings.

• Photophysical Properties:

  • Likely exhibits fluorescence due to extended π-conjugation (potential use in optoelectronic materials).

• Stability:

  • Stable under inert conditions but may degrade under prolonged light/heat exposure.

Applications & Research Interest:

• Medicinal Chemistry:

  • Similar structures are explored for kinase inhibition, anticancer, or antimicrobial activity.

• Material Science:

  • Potential use in organic semiconductors or fluorescent probes due to its conjugated system.

Safety & Handling:

• Toxicity: Limited data; handle with standard precautions (avoid inhalation, skin contact).

• Storage: Store in a cool, dark place under inert atmosphere if sensitive to oxidation.