119491-08-6

Basic information

• Product Name: 1-PROPYL-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 1-PROPYL-1H-INDOLE-3-CARBALDEHYDE;TIMTEC-BB SBB010758;1-propyl-3-indolecarboxaldehyde;1-propylindole-3-carbaldehyde
• CAS NO: 119491-08-6
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.24
• Mol File: 119491-08-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 65-66.5 °C
• Boiling Point: 339.8±15.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-PROPYL-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PROPYL-1H-INDOLE-3-CARBALDEHYDE(119491-08-6)
• EPA Substance Registry System: 1-PROPYL-1H-INDOLE-3-CARBALDEHYDE(119491-08-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 119491-08-6(Hazardous Substances Data)

Usage

Molecular Weight

183.23 g/mol The relative molecular mass of the compound, based on the atomic weights of the constituent elements.

Structure

An indole ring with a carbaldehyde group attached to a propyl chain This describes the basic architecture of the compound, which consists of a five-membered indole ring fused to a six-membered ring, with a propionaldehyde group (a carbonyl group with two hydrogen atoms and a propyl chain attached) connected to the indole ring.

Versatile Building Block in Organic Synthesis

1-Propyl-1H-indole-3-carbaldehyde is used as an intermediate in the production of various chemicals, including pharmaceuticals, agrochemicals, and other fine chemicals This highlights the compound's importance in the synthesis of a wide range of products due to its reactive functional groups and stability.

Pharmacological Activities

Antitumor, antimicrobial, and antioxidant properties The compound has been investigated for its potential therapeutic effects, which include fighting cancer, inhibiting the growth of microorganisms, and neutralizing harmful free radicals.

Key Component in the Fragrance Industry

Used to create floral and earthy scents in perfumes and personal care products 1-Propyl-1H-indole-3-carbaldehyde is valued in the fragrance industry for its unique scent profile, which can be utilized to develop various aromas for consumer products.

Upstream product

• 16885-94-2 1-propyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 120-72-9 indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 106-94-5 propyl bromide 
• 107-08-4 1-iodo-propane 

Relevant articles and documents

Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones

Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two

Novel [(N-alkyl-3-indolylmethylene)hydrazono]oxindoles arrest cell cycle and induce cell apoptosis by inhibiting CDK2 and Bcl-2: synthesis, biological evaluation and in silico studies

As a continuation for our previous work, a novel set of N-alkylindole-isatin conjugates (7, 8a–c, 9 and 10a–e) is here designed and synthesised with the prime aim to develop more efficient isatin-based antitumor candidates. Utilising the SAR outputs from the previous study, our design here is based on appending four alkyl groups with different length (ethyl and n-propyl), bulkiness (iso-propyl) and unsaturation (allyl) on N-1 of indole motif, with subsequent conjugation with different N-unsubstituted isatin moieties to furnish the target conjugates. As planned, the adopted strategy achieved a substantial improvement in the growth inhibitory profile for the target conjugates in comparison to the reported lead VI. The best results were obtained with N-propylindole –5-methylisatin hybrid 8a which displayed broad spectrum anti-proliferative action with efficient sub-panel GI50 (MG-MID) range from 1.33 to 4.23 μM, and promising full-panel GI50 (MG-MID) equals 3.10 μM, at the NCI five-dose assay. Also, hybrid 8a was able to provoke cell cycle disturbance and apoptosis in breast T-47D cells as evidenced by the DNA flow cytometry and Annexin V-FITC/PI assays. Furthermore, hybrid 8a exhibited good inhibitory action against cell cycle regulator CDK2 protein kinase and the anti-apoptotic Bcl-2 protein (IC50= 0.85 ± 0.03 and 0.46 ± 0.02 μM, respectively). Interestingly, molecular docking for hybrid 8a in CDK2 and Bcl-2 active sites unveiled that N-propyl group is involved in significant hydrophobic interactions. Taken together, the results suggested conjugate 8a as a promising lead for further development and optimisation as an efficient antitumor drug.

Visible-Light-Mediated α-Oxygenation of 3-(N,N-Dimethylaminomethyl)-Indoles to Aldehydes

The visible-light-mediated oxygenation of 3-N,N-(dimethylaminomethyl)-indoles bearing various substituents afforded a series of 3-carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)-vincorine is described as well.