Indole-3-carboxaldehyde
[CAS# 487-89-8]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: Indole-3-carboxaldehyde
• Synonyms: 3-Indolealdehyde; 1H-Indole-3-carboxaldehyde
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• CAS Registry Number: 487-89-8
• EC Number: 207-665-8
• SMILES: C1=CC=C2C(=C1)C(=CN2)C=O

Properties

• Melting point: 193-198 ºC
• Flash point: 240 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Indole-3-carboxaldehyde* is an important compound in organic chemistry and biological research. Its unique structure and reactivity make it a valuable tool in a variety of scientific disciplines.

Indole-3-carboxaldehyde, with the molecular formula C10H7NO, was first synthesized in the early 20th century. It is derived from indole, a heterocyclic compound with a fused benzene and pyrrole ring system. The synthesis involves the formylation of indole using reagents such as formic acid and a suitable catalyst.

Indole-3-carboxaldehyde is characterized by the aldehyde group attached to the 3-position of the indole ring. This structure gives it a unique chemical reactivity, particularly its ability to participate in condensation reactions and its role as a key intermediate in a variety of chemical transformations.

Indole-3-carboxaldehyde is a versatile intermediate in synthetic organic chemistry. It is used to produce a variety of indole derivatives through reactions such as condensation and cyclization. These derivatives are useful in pharmaceuticals and agrochemicals.

In medicinal chemistry, indole-3-carboxaldehyde is a precursor for the synthesis of biologically active compounds. Its derivatives are explored for their potential therapeutic properties, including anti-inflammatory and anticancer activities. Research on these derivatives aims to develop new drugs and therapeutic options.

In biological research, indole-3-carboxaldehyde is used as a probe to study enzyme activities and metabolic pathways involving indole compounds. Its role in plant biology and its effects on plant growth regulation are of particular interest. The compound is involved in the synthesis of various plant hormones, including auxins.

The aldehyde group in indole-3-carboxaldehyde makes it useful in chemical sensing applications, where it can interact with a variety of biomolecules and environmental substances, providing the basis for sensors that detect specific analytes through changes in the chemical behavior of the compound.

In materials science, indole-3-carboxaldehyde is used to synthesize functional materials with specific electronic and optical properties. These materials can be used in organic electronics and optoelectronics, including sensors and light-emitting devices.

Indole-3-carboxaldehyde is able to participate in a variety of chemical reactions, making it a versatile reagent in synthetic and applied chemistry. The role of this compound in plant biology and its potential therapeutic applications highlight its importance in biological research and drug development. The presence of the aldehyde group allows for a variety of functionalizations, resulting in a wide range of chemical derivatives with various properties.

References

2020. Glutathione S-transferase: a versatile protein family. 3 Biotech, 10(7).
DOI: PMC7320970

2021. Design, synthesis and biological evaluation of N-substituted indole-thiazolidinedione analogues as potential pancreatic lipase inhibitors. Chemical Biology & Drug Design, 98(2).
DOI: 33864339

2007. Synthesis, characterization and antiamoebic activity of new indole-3-carboxaldehyde thiosemicarbazones and their Pd(II) complexes. European Journal of Medicinal Chemistry, 42(10).
DOI: 17442460