111480-86-5

Basic information

• Product Name: 1-ALLYL-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: ASISCHEM R39437;1-ALLYL-1H-INDOLE-3-CARBALDEHYDE;1-allyl-3-indolecarboxaldehyde;1-allylindole-3-carbaldehyde;1-prop-2-enylindole-3-carbaldehyde
• CAS NO: 111480-86-5
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.22
• Mol File: 111480-86-5.mol
• Article Data: 26

Chemical Properties

• Melting Point: 73-74 °C
• Boiling Point: 339.2 °C at 760 mmHg
• Flash Point: 158.9 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 9.35E-05mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: 1-ALLYL-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ALLYL-1H-INDOLE-3-CARBALDEHYDE(111480-86-5)
• EPA Substance Registry System: 1-ALLYL-1H-INDOLE-3-CARBALDEHYDE(111480-86-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 111480-86-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 1577, 1994 DOI: 10.1021/jo00085a053

InChI:InChI=1/C12H11NO/c1-2-7-13-8-10(9-14)11-5-3-4-6-12(11)13/h2-6,8-9H,1,7H2

Upstream product

• 624-67-9 Propargylic aldehyde 
• 117531-28-9 N-allyl-N-(phenyl)hydroxylamine 
• 487-89-8 Indole-3-carboxaldehyde 
• 106-95-6 allyl bromide 
• 16886-08-1 1-allylindole 
• 100-97-0 hexamethylenetetramine 
• 68-12-2 N,N-dimethyl-formamide 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 120-72-9 indole 
• 557-40-4 Allyl ether 
• 107-18-6 allyl alcohol 
• 75-50-3 trimethylamine 
• 50-00-0 formaldehyd 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 

Downstream Products

• 1257094-97-5 (Z)-3-((1-allyl-1H-indol-3-yl)methylene)-1-(2,6-dichlorophenyl)indolin-2-one 

Relevant articles and documents

Biological activities of pyrazoline-indole based Re(I) carbonyls: DNA interaction, antibacterial, anticancer, ROS production, lipid peroxidation, in vivo and in vitro cytotoxicity studies

Hetero mononuclear rhenium(I) metal complexes (I-V) using different substituted indole-pyrazoline based ligands were synthesized and characterized by spectroscopic and analytical methods. The binding of the rhenium complexes to Herring sperm DNA was monitored by UV spectroscopy, viscosity measurements, and molecular docking studies; groove binding was suggested as the most possible mode and the DNA-binding constants of the complexes were evaluated. In vivo and in vitro cytotoxicity of compounds were evaluated against the brine shrimp and S. cerevisiae cells. An antimicrobial study was carried out by estimating MIC (Minimum Inhibitory Concentration) against two Gram-positive and three Gram-negative bacteria. All synthesized complexes are biologically more active than the corresponding ligands. The anti-proliferation activity of complexes was evaluated on MCF-7, HCT116, and A549 cancer cells by MTT assay. The toxicity profile of synthesized compounds was confirmed by H2O2 production by reactive oxygen species. The increased concentration of lipid peroxidation end products increased free radicals, which enhancing the oxidative stress level in living organisms and results in cell death.

Ultrasound-assisted synthesis and photophysical investigation of a heterocyclic alkylated chalcone: a sensitive and selective fluorescent chemosensor for Fe3+ in aqueous media

Alkylated pyridine chalcone (AIPO) has been synthesized by reaction of 1-allyl-1H-indole-3-carbaldehyde with 2-acetyl pyridine. The chalcone structure was characterized by spectral and elemental analysis. The absorption and emission in ten solvents with different polarities were used to calculate the photophysical parameters for this compound. This heterocyclic fluorescent compound serves as a selective probe for recognition of Fe3+. A 1:1 bonding stoichiometry between AIPO and Fe3+ has been detected by Benesi–Hildebrand, Stern–Volmer and Job-plot methods. The binding stoichiometric ratio was further confirmed by the density functional theory (DFT) calculations.

The Selective Nickel-Catalyzed N-Allylation of C3-Unprotected Indoles under Mild and Clean Conditions

A simple salt free and selective N-allylation of indoles with allylic alcohols has been developed. The protocol uses a catalytic amount of a nickel complex generated in situ from Ni(cod)2 and dppf as diphosphine. The use of DMSO as the reaction solvent is crucial to control the regioselectivity of the reaction with the exclusive formation of the N-allyl product among up to three possible products.

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.