19012-03-4

Basic information

• Product Name: 1-Methylindole-3-carboxaldehyde
• Synonyms: TIMTEC-BB SBB010057;RARECHEM AH BS 0121;1 METHYLINDOLE-3-ALDEHYDE;1-METHYLINDOLE-3-CARBALDEHYDE;1-METHYLINDOLE-3-CARBOXALDEHYDE;1-METHYL-1H-INDOLE-3-CARBALDEHYDE;1-METHYL-1H-INDOLE-3-CARBOXALDEHYDE;AKOS JY2082515
• CAS NO: 19012-03-4
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 242-750-3
• Product Categories: ALDEHYDE;Indoles and derivatives;Indole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles;Heterocycles;Heterocycle-Indole series
• Mol File: 19012-03-4.mol
• Article Data: 134

Chemical Properties

• Melting Point: 70-72 °C(lit.)
• Boiling Point: 318.7 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: Light yellow to orange or brown/Crystalline Powder and Chunks
• Density: 1.1 g/cm³
• Vapor Pressure: 0.000356mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 121302
• CAS DataBase Reference: 1-Methylindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methylindole-3-carboxaldehyde(19012-03-4)
• EPA Substance Registry System: 1-Methylindole-3-carboxaldehyde(19012-03-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 19012-03-4(Hazardous Substances Data)

Usage

Description

1-Methylindole-3-carboxaldehyde is a heterocyclic indole aldehyde characterized by its light yellow to orange or brown crystalline powder appearance. It is known for its ability to form Schiff bases upon condensation with 2-hydroxybenzohydrazide.

Uses

1-Methylindole-3-carboxaldehyde is used as a versatile reactant in various chemical synthesis processes across different industries. Its applications include:
Used in Pharmaceutical Industry:
1-Methylindole-3-carboxaldehyde is used as a reactant for the synthesis of α-ketoamides, which serve as inhibitors of Dengue virus protease, exhibiting antiviral activity in cell-culture.
Used in Chemical Synthesis:
1-Methylindole-3-carboxaldehyde is used as a reactant for the preparation of nitroolefins and β-nitroalcohols via microwaveor ultrasound-assisted Henry reactions. It is also utilized in the synthesis of quinolinones through a three-component Ugi reaction, and in the preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins.
Used in Material Science:
1-Methylindole-3-carboxaldehyde is used as a reactant for the preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent. Additionally, it is used in the preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation, which have potential applications as antibacterial agents.
Used in Polymer Synthesis:
1-Methylindole-3-carboxaldehyde may be used in the synthesis of (Z)-3-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile, via base-catalyzed condensation with thiophene-3-acetonitrile. It is also used in the preparation of a monomer required for the synthesis of poly(3-vinyl-1-methylindole), which has potential applications in the development of novel polymers with specific properties.

Synthesis Reference(s)

Tetrahedron, 49, p. 4015, 1993 DOI: 10.1016/S0040-4020(01)89915-4Synthesis, p. 396, 1987 DOI: 10.1055/s-1987-27960

InChI:InChI=1/C10H9NO/c1-11-6-8(7-12)9-4-2-3-5-10(9)11/h2-7H,1H3

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 77-78-1 dimethyl sulfate 
• 603-76-9 1-methylindole 
• 68-12-2 N,N-dimethyl-formamide 
• 39650-82-3 2,2-dimethoxy-1-methylpyrrolidine 
• 74-88-4 methyl iodide 
• 1912-48-7 2-(1-methyl-1H-indol-3-yl)acetic acid 
• 72228-50-3 C₂₀H₂₃NO₂ 
• 75629-54-8 1-methyl-3-(1-pyrrolidinylmethylene)-3H-indolium iodide 
• 75629-45-7 (Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole 
• 153524-80-2 (E)-1-Methyl-3-(β-methoxyvinyl)indole 
• 120-72-9 indole 
• 128746-62-3 2,3-dibromo-1-methyl-1H-indole 
• 18448-47-0 methyl cyclohex-1-ene-1-carboxylate 

Downstream Products

• 30746-33-9 3-(1-methyl-indol-3-yl)-2-phenyl-acrylonitrile 
• 103907-05-7 1-methyl-indole-3-carbaldehyde thiosemicarbazone 
• 27664-09-1 (E)-3-(1-methyl-1H-indol-3-yl)-1-phenylprop-2-en-1-one 
• 27664-10-4 (E)-3-(1-methyl-1H-indol-3-yl)-1-(p-tolyl)prop-2-en-1-one 
• 26303-27-5 1-methyl-indole-3-carbaldehyde phenylhydrazone 
• 27664-11-5 1-(4-methoxy-phenyl)-3-(1-methyl-indol-3-yl)-propenone 
• 6965-44-2 N-Methyl-indole-3-carbinol 
• 31896-75-0 bis(1-methyl-1H-indol-3-yl)methane 
• 41785-91-5 3-(2,6-diphenyl-pyran-4-ylidenemethyl)-1-methyl-indole 
• 119549-99-4 1-(4-Chloro-phenyl)-3-(1-methyl-1H-indol-3-yl)-3-[1,2,4]triazol-1-yl-propan-1-one 
• 141987-22-6 diphenyl(2-hydroxy-2--1-morpholinoethyl)phosphine oxide 
• 7171-84-8 methyl-1 (nitro-2 ethynyl)-3 indole 
• 2731-00-2 1-methyl-3-[(E)-2-nitrovinyl]-1H-indole 
• 143817-19-0 [4-(3,3-Diphenyl-propionyl)-piperazin-1-yl]-(1-methyl-1H-indol-3-yl)-acetonitrile 

Relevant articles and documents

Light- and redox-gated molecular brakes consisting of a pentiptycene rotor and an indole pad

Two photochemically and electrochemically active alkenes 3Me and 3An containing pentiptycene and indole groups have been synthesized and investigated as light and/or redox-gated molecular brakes. The pentiptycene group functions as the four-bladed rotor, the indole group as the brake pad, and the vinylene group as the switch module. The E configuration corresponds to the brake-off state, in which the rotation of the rotor is free with a rotation rate of 108-109 at ambient temperature according to DFT calculations. The Z configuration corresponds to the brake-on state, in which the rotation rate is decreased to 101-102, depending on the N-substituent of indole, according to line-shape analysis of variable temperature 13C NMR spectra. The overall braking effect reaches a factor of 106-108. While the combined photochemical E → Z and electrochemical Z → E switching has a higher capacity than the two-way photochemical switching in the case of 3Me, the switching capacity are comparable for the two methods in 3An. The results also show that photochemical E-Z isomerization is much more reliable than the electrochemical counterpart, as the stability of the redox intermediates plays a critical role in determining the robustness of the molecular brakes via electrochemical switching. The photochemical and/or electrochemical switching between the E and Z isomers of two alkenes substituted with both pentiptycene and indole groups results in a change of the rotation rate as large as 106-108 fold for the pentiptycene group about the pentiptycene-vinylene C-C bond, corresponding to a new generation of light- and redox-gated molecular brakes.

Synthesis of a photostable energy-transfer pair for dNA traffic lights

A new cyano-substituted thiazole red derivative as a red emitter and a novel green fluorescent donor dye of the cyanine styryl type were synthesized in good yields. Characterization of their optical properties revealed excellent photostabilities and large apparent Stokes' shifts. Both dyes can be incorporated into oligonucleotides through postsynthetic click -type chemistry and combined in a diagonal arrangement in double-stranded DNA. As a result, both dyes combine to an energy-transfer pair in DNA that shows remarkable optical properties such as significant emission wavelength shift from green to red upon hybridization owing to high energy-transfer efficiency between the two dyes and remarkable emission red/green color contrast ratio. The combination of these dyes as an energy-transfer pair according to our concept of DNA traffic lights has high potential for applications in molecular imaging.

Intramolecular alkylations of aromatic compounds, XXII: Synthesis of cis-1,6,10-trimethyl-1,2,3,4,5,6,7,8,9,10-decahydroindolo(4,3-fg)quinoline, a new approach to the ergolen framework

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Synthesis of Analogues of Indole Alkaloids from Sea Sponges – Aplysinopsins by the Reaction of Amines with (4Z)-4-[(1H-indol-3-yl)-methylene]-1,3-oxazol-5(4H)-ones

A new two-step approach toward the synthesis of aplysinopsin analogues 5-(1-R-1H-indol-3-ylmethylene)-2-aryl-3,5-dihydroimidazol-4-ones consisting in obtaining and reaction of 4-(1-R-1H-indol-3-ylmethilene)-2-Ar-4H-oxazol-5-ones with amines was developed. The configuration of starting compounds and final products was determined by13С and1H-nmr spectroscopy.

Amphiphilic Cyanine-Platinum Conjugates as Fluorescent Nanodrugs

Two fluorescent nanomedicines based on small molecular cyanine-platinum conjugates have been prepared via a nanoprecipitation method and characterized by transmission electron microscopy (TEM) as well as dynamic light scattering (DLS). The conjugates exhibited an enhanced fluorescence in their nanoparticle formulation compared to that in solution. The nanomedicines could be endocytosed by cancer cells as revealed by confocal laser scanning microscopy (CLSM) and showed high cellular proliferation inhibition. Fluorescent platinum nanomedicines prepared directly from small molecules could be an alternative strategy for developing new drugs with simultaneous cellular imaging and cancer therapy functions.

Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.

Design, synthesis and biological evaluation of N-substituted indole-thiazolidinedione analogues as potential pancreatic lipase inhibitors

Pancreatic Lipase (PL) is a key enzyme responsible for the digestion of 50%–70% of dietary triglycerides, hence its inhibition is considered as a viable approach for the management of obesity. A series of indole-TZD hybrid analogues were synthesized, characterized and evaluated for their PL inhibitory activity. Knoevenagel condensation of various substituted indole-3-carboxaldehyde with substituted thiazolidinediones resulted in the formation of titled analogues. Analogues 6d and 6e exerted potent PL inhibitory activity (IC50-6.19 and 8.96?μM, respectively). Further, these analogues exerted a competitive mode of PL inhibition. Moreover, molecular modelling studies were in agreement with the in vitro results (Pearson's r?=.8682, p?.05). The fluorescence spectroscopic analysis further supported the strong binding affinity of these analogues with PL. A molecular dynamics study (20?ns) indicated that these analogues were stable in a dynamic environment. Thus, the present study highlighted the potential role of indole-thiazolidinedione hybrid analogues as potential PL inhibitors and further optimization might result in the development of new PL inhibitory lead candidates.

One-Pot Multi-Component Synthesis and Biological Evaluation of Novel Indole-Pyrimidine Derivatives as Potent Anti-Cancer and Anti-Microbial Agents

Abstract: A series of novel hybrids of indole-pyrimidine moieties were synthesized and evaluated for their in?vitro anti-cancer, in vitro anti-bacteria and in vitro anti-fungal activities. The results showed that most of these compounds possessed significant cytotoxic potency against four cancer cell lines, HeLa, HEK 293T and MCF-7. The compounds 4-(3-(benzyloxy)phenyl)-6-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine,4-(4-chlorophenyl)-6-(1-methyl-1H-indol-3-yl) pyrimidin-2-amine and4-(1H-indole-3-yl)-6-phenylpyrimidin-2-amine showed good activity against HEK 293T. The compounds 4-(3-(benzyloxy)phenyl)-6-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine and 4-(4-chlorophenyl)-6-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine showed good to moderate activity against MCF-7, whereas compound 4-(3-(benzyloxy)phenyl)-6-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine exhibit moderate activity against HaLa S3 cell line. The newly synthesized derivatives were also screened for their in vitro anti-bacterial activity against Bacillus subtilis, B. megatherium, B.?pumilis, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter aerogenes, Streptococcus pyogenes, Staphylococcus aureus, Proteus vulgaris, Escherichia coli, using streptomycin as a standard drug. Among tested compound 4-(3-(benzyloxy)phenyl)-6-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine shows more potent activity compared to standard, where as the remaining analogues exhibited well to moderate activity compared to standard. Anti-fungal screening results suggest that the compound 4-(4-chlorophenyl)-6-(1H-indol-3-yl)pyrimidin-2-amineshowed potent activity against Dreschleria halides. The remaining compounds showed nearest activity against all the tested fungal strains compared to standard drug.