Indole-3-carbaldehyde

Indole-3-carbaldehyde (also known as I3A or 3-formylindole) is a naturally occurring organic compound that is a derivative of the heterocycle indole. It is a pale yellow solid that is sparingly soluble in water but more so in organic solvents.

Structure and Properties

Indole-3-carbaldehyde is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of a pyrrole ring fused to a benzene ring. The structure of indole-3-carbaldehyde is characterized by a three-membered ring of two carbon atoms and one nitrogen atom, attached to a benzene ring at one end and a formyl group (-CHO) at the other.

The molecular formula of indole-3-carbaldehyde is C9H7NO. It has a molar mass of 145.16 g/mol and a density of 1.186 g/cm3. Its melting point is 54-56 °C and its boiling point is 281-282 °C.

Synthesis

Indole-3-carbaldehyde can be synthesized from indole via Vilsmeier-Haack reaction, a formylation reaction that uses a combination of phosphorus oxychloride and dimethylformamide.

Applications

Indole-3-carbaldehyde has been used in various scientific researches due to its biological activities. It has been used as a starting material in the synthesis of various indole derivatives with potential therapeutic applications. For example, it has been used in the synthesis of indole-based antimicrobial agents, antioxidants, and anticancer agents.

Safety

As with all chemicals, indole-3-carbaldehyde should be handled with care. It may cause skin and eye irritation, and may be harmful if swallowed or inhaled.

See Also

• Indole
• Vilsmeier-Haack reaction
• Organic compound
• Antimicrobial
• Antioxidant
• Anticancer