1193-59-5

Usage

Uses

Used in Fragrance and Flavor Industry:
1,5-dimethyl-1H-pyrrole-2-carbaldehyde is used as a key ingredient in the creation of fragrances and flavors due to its distinct and characteristic odor, enhancing the sensory experience of various consumer products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1,5-dimethyl-1H-pyrrole-2-carbaldehyde serves as an intermediate in the synthesis of biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Similarly, in agrochemicals, 1,5-dimethyl-1H-pyrrole-2-carbaldehyde(SALTDATA: FREE) is utilized as an intermediate, playing a crucial role in the synthesis of compounds that can be used in pest control and crop protection, thereby supporting agricultural productivity.
Used in Materials Science:
1,5-dimethyl-1H-pyrrole-2-carbaldehyde also has potential applications in materials science, particularly in the development of organic semiconductor materials, where it can contribute to advancements in electronic and optoelectronic devices.

InChI:InChI=1/C7H9NO/c1-6-3-4-7(5-9)8(6)2/h3-5H,1-2H3

Upstream product

• 1192-79-6 formyl-2 methyl-5 pyrrole 
• 77-78-1 dimethyl sulfate 
• 1192-58-1 N-methylpyrrole aldehyde 
• 74-88-4 methyl iodide 
• 56341-36-7 1,5-dimethyl-1H-pyrrole-2-carbonitrile 
• 930-87-0 1,2,5-trimethyl-1H-pyrrole 
• 600-29-3 1,2-dimethylpyrrole 
• 75-27-4 bromodichloromethane 

Downstream Products

• 134789-87-0 2-(1,5-Dimethyl-1H-pyrrol-2-yl)-4,5-bis-(4-methoxy-phenyl)-1H-imidazole 

Relevant academic research and scientific papers

Lithiation of Heterocycles Directed by α-Amino Alkoxides

The addition of heterocyclic aromatic aldehydes to certain lithium dialkylamides gave α-amino alkoxides that were ring-lithiated with butyllithium.Alkylation and hydrolysis provided ring-substituted heterocyclic aromatic aldehydes via a one-pot reaction.The metalation of α-amino alkoxides derived from thiophenecarboxaldehydes, furaldehydes, N-methylpyrrolecarboxaldehydes, and indolecarboxaldehydes was examined.The regioselectivity of the lithiation, was dependent on the heterocycle, the amine component of the α-amino alkoxide, and the metalation conditions.A novel N-methyl metalation of α-amino alkoxides derived from N-methylpyrrole-2-carboxaldehyde and N-methylindole-2-carboxaldehyde was achieved when N,N,N'-trimethylethylenediamine was used as the amine component for in situ formation of the α-amino alkoxides.The novel directed N-methyl lithiations are attributed to an intramolecular TMEDA-like assisted metalation.

Contribution of pyrrole formation and polymerization to the nonenzymatic browning produced by amino-carbonyl reactions

Recent studies have hypothesized that pyrrole formation and polymerization may be contribute to the nonenzymatic browning produced in both oxidized lipid/protein reactions and the Maillard reaction. To develop a methodology that would allow investigation of the contribution of this browning mechanism, the kinetics of formation of color, fluorescence, and pyrrolization in 4,5(E)-epoxy-2(E)-heptenal/lysine and linolenic acid/lysine model systems were studied. In both cases similar kinetics for the three measurements were observed at the two temperatures assayed (37 and 60 °C), and there was a high correlation among color, fluorescence, and pyrrolization measurements obtained as a function of incubation time. Because the color and fluorescence production in the 4,5(E)-epoxy-2(E)-heptenal/lysine system is a consequence of pyrrole formation and polymerization, the high correlations observed with the unsaturated fatty acid also suggest a contribution of the pyrrole formation and polymerization to the development of color and fluorescence observed in the fatty acid/lysine system. Although the contribution of other mechanisms cannot be discarded, all of these results suggest that when the pyrrole formation and polymerization mechanism contributes to the nonenzymatic browning of foods, a high correlation among color, fluorescence, and pyrrolization measurements should be expected.

Copper-Catalyzed Three-Component Formal [3 + 1 + 2] Benzannulation for Carbazole and Indole Synthesis

Three-component formal [3 + 1 + 2] benzannulation reactions of indole-3-carbaldehydes or 1-methyl-pyrrole-2-carbaldehydes with two different molecules of saturated ketones have been successfully developed under Cu-catalyzed and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated conditions. Various unsymmetrically substituted carbazoles and indoles were obtained up to 95% yield. Furthermore, the resulting products exhibit unusual aggregation-induced emission (AIE) properties in the solid state. This method features high atom-economy, cheap catalysts and oxidants, wide substrate scope, and saturated ketones as one-carbon and two-carbon sources, thus providing an efficient approach to polycyclic carbazole and indole compounds.

Thermal Behavior Analysis of Two Synthesized Flavor Precursors of N-alkylpyrrole Derivatives

To expand the library of pyrrole-containing flavor precursors, two new flavor precursors—methyl N-benzyl-2-methyl-5-formylpyrrole-3-carboxylate (NBMF) and methyl N-butyl-2-methyl-5-formylpyrrole-3-carboxylate (NUMF)—were synthesized by cyclization, oxidation, and alkylation reactions. Thermogravimetry (TG), differential scanning calorimeter, and pyrolysis–gas chromatography/mass spectrometry were utilized to analyze the thermal degradation behavior and thermal degradation products of NBMF and NUMF. The TG-DTG curve indicated that the maximum mass loss rates of NBMF and NUMF appear at 310 and 268°C, respectively. The largest peaks of NBMF and NUMF showed by the differential scanning calorimeter curve were 315 and 274°C, respectively. Pyrolysis–gas chromatography/mass spectrometry detected small molecule fragrance compounds appeared during thermal degradation, such as 2-methylpyrrole, 1-methylpyrrole-2-carboxylic acid methyl ester, limonene, and methyl formate. Finally, the thermal degradation mechanism of NBMF and NUMF was discussed, which provided a theoretical basis for their application in tobacco flavoring additives.

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.

Copper-catalyzed aerobic methyl/methylene oxygenation and C-H formylation with a DABCO-DMSO system for the synthesis of carbonyl indoles and pyrroles

Copper-catalyzed aerobic methyl/methylene oxygenation of substituted indoles and pyrroles was developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an additive in dimethyl sulfoxide (DMSO). Similar aerobic catalytic conditions could also be utilized for direct C-H formylation of C(3) on indoles and C(2) on pyrroles.

An N.M.R. Investigation of Ground-State Polarization of Some Substituted Aromatic Systems

The previously established n.m.r. method for estimating mobile bond orders was applied to the investigation of ground-state polarization of benzene derivatives with ortho or para pairs of +R/-R substituents, naphthalene and five heteroaromatic systems (furan, thiophen, pyrrole, quinoline and pyrazole).Evidence for significant ground-state polarization which is solvent-independent was found in a number of these systems, especially benzene, pyrrole and pyrazole.