129445
Indole-3-carboxaldehyde
97%
Synonym(s):
β-Indolylaldehyde, 3-Formylindole, 3-Indolylformaldehyde, Indole-3-carbaldehyde, NSC 10118
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About This Item
Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
Molecular Weight:
145.16
Beilstein/REAXYS Number:
114117
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
97%
form
solid
mp
193-198 °C (lit.)
functional group
aldehyde
SMILES string
O=Cc1c[nH]c2ccccc12
InChI
1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI key
OLNJUISKUQQNIM-UHFFFAOYSA-N
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General description
Indole-3-carboxaldehyde can undergo Schiff bases condensation to form multifunctional silica nano-vehicles and magnetic nanoparticles.
Application
Indole-3-carboxaldehyde was used to prepare analogs of the indole phytoalexin cyclobrassinin with NR1R2 group. It was also used as the starting material for the synthesis of higher order indoles including isoindolo[2,1-a]indoles, aplysinopsins, and 4-substituted-tetrahydrobenz[cd]indoles.
Reactant for preparation of:
- Analgesic agents
- Hypoglycemic agents
- Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Antibacterial and antifungal agents
- Antiamoebic and cytotoxic agents
- Inhibitors of the Dengue virus protease with antiviral activity in cell-culture
- Curcumin analogues as possible anti-proliferative & anti-inflammatory agents
- Inhibitors of Bcl-2 family proteins
- Inhibitors of the C-terminal domain of RNA Polymerase II as antitumor agents
- Inhibitors of TNF-α and IL-6 with anti-tubercular activity
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Colloids and surfaces. B, Biointerfaces, 114, 158-163 (2013-11-05)
Multifunctional silica nano-vehicles (SiO2@indol-IL) and magnetic nanoparticles (Fe3O4@indol-IL) were constructed through the Schiff bases condensation of indole-3-carboxaldehyde and 4-acetyl-N-allyl pyridinium chloride (ILs) with the amine groups of silica and magnetic nanoparticles. SiO2@indol-IL can inhibit the proliferation of HepG-2 cells in
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European journal of medicinal chemistry, 43(1), 160-165 (2007-05-29)
Eight novel heterocyclic Schiff bases derived from the condensation reactions of indole 3-carboxaldehyde with different l-amino acids (histidine, glutamic acid, aspartic acid, leucine, valine) as well as with some aminophenols, have been synthesized and characterized by various spectroscopic methods (IR
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European journal of medicinal chemistry, 46(12), 6112-6118 (2011-10-22)
A rapid, efficient and environmental benign methodology for the preparation of 2,5-disubstituted indole analogues is developed. 2,5-Disubstituted indole-3-carboxaldehydes (1a-c) undergo Knoevenagel condensation with barbiturates (2 &4), thiazolidine-2,4-dione (6) and 3-methyl-1H-pyrazol-5(4H)-one (8) in solvent-free, NH(4)OAc catalyzed, microwave assisted reaction. Structures of
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