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 
• 75-18-3 dimethylsulfide 
• 72010-39-0 N-methyl-N-[(1-methyl-1H-indol-3-yl)methylene]methanaminium chloride 
• 603-76-9 1-methylindole 
• 1067241-18-2 N,O-dimethylindole 
• 616-38-6 carbonic acid dimethyl ester 
• 75629-45-7 (Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole 
• 120-72-9 indole 
• 108-05-4 vinyl acetate 
• 459869-41-1 Se-phenyl 1-methyl-3-indolecarboselenoate 
• 18448-47-0 methyl cyclohex-1-ene-1-carboxylate 
• 128746-62-3 2,3-dibromo-1-methyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 74-88-4 methyl iodide 

Downstream Products

• 1174639-37-2 (E)-N-[(1-methyl-1H-indol-3-yl)methylidene]aniline 
• 1255528-22-3 N-((1-methyl-1H-indol-3-yl)methylene)-1,1-diphenylmethanamine 
• 1280185-91-2 2-(2-benzoylphenylamino)-2-(1-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide 
• 1280185-93-4 2-(3-cyano-2-oxo-4-phenylquinolin-1(2H)-yl)-2-(1-methyl-1H-indol-3-yl)-N-(pentan-2-yl)acetamide 
• 1284312-35-1 3-phenyl-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-36-2 3-(4'-chlorophenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-37-3 3-(4'-fluorophenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-38-4 3-(4'-trifluoromethylphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-39-5 3-(3',4'-dimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-40-8 3-(3',5'-dimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-42-0 3-(4'-benzyloxy-3'-methoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-43-1 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1367777-75-0 1-(2,6-dimethoxyphenyl)-3-(1-methyl-1H-indol-3-yl)prop-2-en-1-one 
• 73393-85-8 1-(2,4-dimethoxyphenyl)-3-(1-methyl-1H-indol-3-yl)prop-2-en-1-one 

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.

Synthesis, in silico studies, and evaluation of syn and anti isomers of n-substituted indole-3-carbaldehyde oxime derivatives as urease inhibitors against helicobacter pylori

Gastrointestinal tract infection caused by Helicobacter pylori is a common virulent disease found worldwide, and the infection rate is much higher in developing countries than in developed ones. In the pathogenesis of H. pylori in the gastrointestinal tract, the secretion of the urease enzyme plays a major role. Therefore, inhibition of urease is a better approach against H. pylori infection. In the present study, a series of syn and anti isomers of N-substituted indole-3-carbaldehyde oxime derivatives was synthesized via Schiff base reaction of appropriate carbaldehyde derivatives with hydroxylamine hydrochloride. The in vitro urease inhibitory activities of those derivatives were evaluated against that of Macrotyloma uniflorum urease using the modified Berthelot reaction. Out of the tested compounds, compound 8 (IC50 = 0.0516 ± 0.0035 mM) and compound 9 (IC50 = 0.0345 ± 0.0008 mM) were identified as the derivatives with potent urease inhibitory activity with compared to thiourea (IC50 = 0.2387 ± 0.0048 mM). Additionally, in silico studies for all oxime compounds were performed to investigate the binding interactions with the active site of the urease enzyme compared to thiourea. Furthermore, the drug-likeness of the synthesized oxime compounds was also predicted.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.