1192-58-1

Usage

Uses

Used in Chemical Synthesis:
N-Methylpyrrole-2-carboxaldehyde is used as a key intermediate in the synthesis of various organic compounds. One of its notable applications is in the preparation of 3-(1-methyl-1H-pyrrol-2-yl)propanoic acid, which is an important building block for the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Methylpyrrole-2-carboxaldehyde is utilized as a starting material for the synthesis of drugs with potential therapeutic applications. Its unique chemical structure allows for the creation of novel molecules that can target specific biological pathways, making it a valuable asset in drug discovery and development.
Used in Flavor and Fragrance Industry:
Due to its distinct chemical properties, N-Methylpyrrole-2-carboxaldehyde is also used in the flavor and fragrance industry. It can be employed to create unique scents and flavors for various consumer products, such as perfumes, cosmetics, and the food industry, where it can enhance the sensory experience of the products.
Used in Research and Development:
N-Methylpyrrole-2-carboxaldehyde is a valuable compound in the field of research and development, particularly in the study of organic chemistry and material science. It can be used to explore new reaction pathways, develop innovative synthetic methods, and investigate the properties of novel materials.

InChI:InChI=1/C6H7NO/c1-7-4-2-3-6(7)5-8/h2-5H,1H3

Upstream product

• 96-54-8 N-Methylpyrrole 
• 3724-43-4 Vilsmeier reagent 
• 68-12-2 N,N-dimethyl-formamide 
• 183998-23-4 (1-Methyl-1H-pyrrol-2-yl)-pyrrolidin-1-yl-methanone 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 10025-87-3 trichlorophosphate 
• 35711-34-3 tolmetin sodium 
• 4497-57-8 2,2,4-trimethyl-3,4-dihydroquinoline-1(2H)-carbaldehyde 
• 2700-30-3 N,N-diisorpopylformamide 
• 607-00-1 diphenylformamide 

Downstream Products

• 113370-70-0 methyl N-(N-methylpyrrol-2-ylmethylene)phenylglycinate 
• 86770-99-2 (Z)-α-(p-methylphenyl)-β-(N-methyl-2-pyrrolyl)acrylonitrile 
• 56423-58-6 2-(1-hydroxyethyl)-1-methylpyrrole 
• 79499-42-6 2-(4-methoxybenzyl)-1-methyl-1H-pyrrole 
• 2769-90-6 ethyl (2E)-3-(1-methyl-1H-pyrrol-2-yl)prop-2-enoate 
• 51485-76-8 β-(1-Methyl-2-pyrryl)acrylsaeure 
• 96238-45-8 (Z)-3-(1-methyl-2-pyrrolyl)propenonitrile 
• 96238-37-8 (E)-3-(1-methyl-1H-pyrrol-2-yl)acrylonitrile 
• 143817-21-4 [4-(3,3-Diphenyl-propionyl)-piperazin-1-yl]-(1-methyl-1H-pyrrol-2-yl)-acetonitrile 
• 3783-66-2 1-methyl-2-styryl-pyrrole 
• 2433-77-4 (Z)-1-(1-methyl-2-pyrrolyl)-2-phenylethene 
• 2761-79-7 (E)-1-Methyl-2-(2-phenylethenyl)-1H-pyrrole 
• 24437-41-0 1-methyl-2-pyrroleacetonitrile 
• 69917-84-6 (E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole 

Relevant academic research and scientific papers

Novel yellow- to red-emitting fluorophores: Facile synthesis, aggregation-induced emission, two-photon absorption properties, and application in living cell imaging

Four novel yellow-to red-emitting fluorophores with a 1-(2-hydroxyethyl) pyridinium core and different electron-donating terminal moieties (N-methylcarbazole, N,N-dibutylbenzenamine, N-methylpyrrole, and 2-methylfuran) were designed and facilely synthesized via the one-step Knoevenagel condensation. All these compounds (HPs) were characterized by 1H NMR, 13C NMR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated in various solvents. And the density functional theory calculations were conducted to analyze the electronic structures of HPs. The two-photon absorption cross-sections (δ) values of HPs measured by the Z-scan technique were determined to be as large as 1354 (1HP-CZ), 4462 (2HP-BA), 836 (3HP-PR), and 2944 GM (4HP-FU) in DMSO. The two-photon action cross-sections (Φ × δ) values of 1HP-CZ and 2HP-BA in H2O measured by the two-photon induced fluorescence method were about 50 GM. 1HP-CZ, 3HP-PR, and 4HP-FU also exhibited good water solubility. Meanwhile, it was found that 2HP-BA exhibited notable aggregation-induced emission characteristic in DMSO/H2O mixture. The aggregate particle size distribution of 2HP-BA was measured by the dynamic light scattering method, and the aggregation characteristic of 2HP-BA was observed by the transmission electron microscopy. Besides, 2HP-BA also exhibited red emission. Then, HPs with relatively low cytotoxicity were used for one- and two-photon excited fluorescence imaging in living HepG2 cells. The results indicate that HPs are potential candidates in the bioimaging field due to their photophysical properties and biocompatibility.

A new series of two-photon blue/violet fluorescent trans-alkenes: Green synthesis and optical properties

A new series of trans-alkenes (3a-3e) containing different electron-donating groups were synthesized by the solvent-free Horner-Wadsworth-Emmons reaction, and characterized by infrared, hydrogen nuclear magnetic resonance, mass spectrometry and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. Experimental results show different trends in linear and nonlinear optical properties with different donor units. 3a with triphenylamine donor exhibits the best optical properties. It emits strong blue up-converted fluorescence, and the two-photon absorption cross-section can be as large as 218 GM in DCM.

Preparation and Photophysical Properties of All-trans Acceptor-π-Donor (Acceptor) Compounds Possessing Obvious Solvatochromic Effects

A series of all-trans acceptor-π-donor (acceptor) compounds (BAQ, SFQ, BLQ, and XJQ) were conveniently synthesised and characterised by infrared, nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their photophysical properties, including linear absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence, were systematically investigated. All the compounds show obvious solvatochromic effects, such as significant bathochromic shifts of the emission spectra and larger Stokes shifts in more polar solvents. Under excitation from a femtosecond Ti:sapphire laser with a pulse width of 140 fs, they all exhibit strong two-photon excited fluorescence, and the two-photon absorption cross-sections in THF are 851 (BAQ), 216 (SFQ), 561 (BLQ), and 447 (XJQ) GM respectively. A combination of density functional theory (DFT) and time-dependent density functional theory (TDDFT) approaches was used to investigate the relationships between the structures and the photophysical properties of these compounds. The results show that they may have a potential application as polarity-sensitive two-photon fluorescent probes.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

Serendipitous base catalysed condensation-heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles

A serendipitous discovery of a novel one-pot synthesis of 4,6-disubstituted 5-azaindoles is reported herein. In the presence of Hunig's base, various N-substituted pyrrole-2-carboxaldehydes have been efficiently transformed into their corresponding 4,6-disubstituted 5-azaindoles through an imine mediated cascade condensation-heteroannulation. The synthetic value of the methodology is established by preparing a novel chemical analogue of a cannabinoid receptor type 2 (CB2) agonist.

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

The Murai reaction is a ruthenium-catalyzed transformation leading to alkylated arenes through the C?C bond formation between an alkene and an arene bearing a directing group. Discovered in the nineties, this useful C?H activation based coupling has been the object of intense study since its discovery. After having studied the Murai reaction on 2-formylfurans of biomass derivation, we describe here the carbonylative version applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. This acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes thanks to the installation of removable imine directing groups. The transformation can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120–150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups. (Figure presented.).

Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions

Transition-metal-catalyzed programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero-hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.

Rhenium-Catalyzed Reduction of Carboxylic Acids with Hydrosilanes

Re2(CO)10 efficiently catalyzes the direct reduction of various carboxylic acids under mild conditions (rt, irradiation 350 or 395 nm). While aliphatic carboxylic acids were readily converted to the corresponding disilylacetals with low catalyst loading (0.5 mol %) in the presence of Et3SiH (2.2 equiv), aromatic analogues required more drastic conditions (Re2(CO)10 5 mol %, Ph2MeSiH 4.0 equiv) to afford the corresponding aldehydes after acid treatment.

Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents

Using matrine (1) as the lead compound, a series of new 14-(N-substituted-2-pyrrolemethylene) matrine and 14-(N-substituted-indolemethylene) matrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines (SMMC-7721, A549 and CNE2). The results revealed that compound A6 and B21 displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine) and positive control Cisplatin. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound A6 and B21 could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. The cell cycle analysis also revealed that compound A6 could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase.