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4-Methyl-1H-indole-3-carboxaldehyde
[CAS# 4771-48-6]

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Identification
Classification Organic raw materials >> Heterocyclic compound >> Indoles
Name 4-Methyl-1H-indole-3-carboxaldehyde
Synonyms 4-Methyl-3-indolecarboxaldehyde
Molecular Structure CAS # 4771-48-6, 4-Methyl-1H-indole-3-carboxaldehyde, 4-Methyl-3-indolecarboxaldehyde
Molecular Formula C10H9NO
Molecular Weight 159.18
CAS Registry Number 4771-48-6
EC Number 891-500-5
SMILES CC1=C2C(=CC=C1)NC=C2C=O
Properties
Density 1.2±0.1 g/cm3, Calc.*, 1.226 g/mL (Expl.)
Melting point 192-194 ºC (Expl.)
Index of Refraction 1.699, Calc.*
Boiling Point 347.0±22.0 ºC (760 mmHg), Calc.*
Flash Point 171.6±29.8 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2AH319
Specific target organ toxicity - single exposureSTOT SE3H335
Acute toxicityAcute Tox.4H302
SDS Available
up Discovory and Applicatios
4-Methyl-1H-indole-3-carboxaldehyde is an organic compound with a structure consisting of an indole ring fused with a methyl group and a carboxaldehyde functional group. It is an important intermediate in organic synthesis, particularly in the pharmaceutical and chemical industries. This compound has gained attention due to its unique chemical properties and versatility in various applications, including in the synthesis of complex molecules, organic electronics, and biological research.

The discovery of 4-methyl-1H-indole-3-carboxaldehyde can be traced back to the investigation of indole derivatives, which have been of interest for decades due to their wide range of biological activities. Indole-based compounds are known to possess significant pharmacological properties, including anticancer, antimicrobial, and anti-inflammatory effects. Researchers have focused on modifying the indole structure to improve its activity and selectivity. The introduction of a methyl group at the 4-position of the indole ring, coupled with a carboxaldehyde functional group at the 3-position, led to the development of 4-methyl-1H-indole-3-carboxaldehyde as an interesting compound for further study.

One of the primary applications of 4-methyl-1H-indole-3-carboxaldehyde is in the synthesis of complex organic molecules. The presence of both the methyl group and the aldehyde group makes it a useful building block for the construction of more intricate structures. Its reactivity as an aldehyde allows for the formation of carbon-carbon bonds, and it can undergo various reactions, including condensation and cyclization, to yield bioactive molecules. Researchers have used it as an intermediate in the synthesis of indole derivatives that exhibit a wide range of biological activities, including anti-cancer agents and compounds with potential applications in treating neurological disorders.

In addition to its role in organic synthesis, 4-methyl-1H-indole-3-carboxaldehyde is also being explored for its potential in organic electronics. Indole derivatives have shown promise as materials for organic semiconductors due to their ability to conduct electricity and their stability in thin-film applications. The compound’s structure makes it a candidate for use in organic light-emitting diodes (OLEDs) and organic solar cells (OSCs), where it can contribute to efficient charge transport and light emission.

Furthermore, 4-methyl-1H-indole-3-carboxaldehyde has potential applications in biological research, particularly in the development of fluorescent probes and sensors. The compound’s ability to absorb light at specific wavelengths and its reactivity with other molecules make it suitable for use in fluorescence-based assays, where it can help detect and quantify biological targets or environmental conditions. Researchers are also investigating its role in the development of inhibitors or activators of specific enzymes, which could lead to novel therapeutic strategies.

In conclusion, 4-methyl-1H-indole-3-carboxaldehyde is an important compound with a broad range of applications, from organic synthesis to organic electronics and biological research. Its discovery has opened new avenues for the design and development of novel molecules with therapeutic potential, as well as materials for advanced electronic devices. As research continues, the compound’s versatility and reactivity are likely to lead to further innovations in various fields.
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