69687-80-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2,5-dimethylpyrrole-3-carboxylate is used as a chemical precursor for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Organic Chemistry Research:
Methyl 2,5-dimethylpyrrole-3-carboxylate is used as a key intermediate in the synthesis of complex organic molecules. Its reactivity and functional groups make it a valuable building block for researchers in the field of organic chemistry.
Used in Chemical Synthesis:
Methyl 2,5-dimethylpyrrole-3-carboxylate is used as a versatile reagent in the synthesis of a variety of organic compounds. Its carboxylic ester group can participate in various chemical reactions, enabling the formation of a diverse array of products.

InChI:InChI=1/C8H11NO2/c1-5-4-7(6(2)9-5)8(10)11-3/h4,9H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 57338-76-8 2,5-dimethyl-1H-pyrrole-3-carboxylic acid 
• 105-45-3 acetoacetic acid methyl ester 
• 78-95-5 chloroacetone 
• 67271-63-0 4-cyano-2,5-dimethyl-pyrrole-3-carboxylic acid ethyl ester 
• 34034-36-1 2-methyl-5-formylpyrrole-3-carboxylic acid methyl ester 
• 1286715-92-1 C₈H₁₃NO₃ 

Downstream Products

• 175205-91-1 4-formyl-2,5-dimethyl-pyrrole-3-carboxylic acid methyl ester 
• 144782-92-3 methyl 4-(2-((4-fluorophenyl)methyl)benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 144782-93-4 methyl 4-<2-(2,5-difluorobenzyl)benzoyl>-2,5-dimethylpyrrole-3-carboxylate 
• 144782-91-2 4-(2-chloromethylbenzoyl)pyrrole 
• 111596-03-3 methyl 4-(2-iodobenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 154138-59-7 methyl 4-(2-bromo-4-fluorobenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 144782-90-1 4-(4-Chloro-benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 111596-15-7 4-(2-Methoxy-benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 111595-98-3 4-(2,4-Dichloro-benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 144782-94-5 2,5-Dimethyl-4-[2-(4-methyl-benzyl)-benzoyl]-1H-pyrrole-3-carboxylic acid methyl ester 
• 111596-00-0 4-(2-Fluoro-benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and pyrolysis of two novel pyrrole ester flavor precursors

In order to develop the high-temperature-released pyrrole aroma, two novel flavors precursors of methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate and methyl 2-methyl-5-(((2-methylbutanoyl)oxy)methyl)-1-propyl-1H-pyrrole-3-carboxylate were synthesized using glucosamine hydrochloride and methyl acetoacetate as raw materials through cyclization, oxidation, alkylation, reduction, and esterification. The target compounds were characterized by nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). Thermogravimetry (TG), differential scanning calorimeter (DSC) and the pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) methods were used to analyze the heating-stability of the target compounds, and the pyrolysis mechanism was inferred. Py-GC/MS results indicated that some fragrance compounds were formed during?thermal degradation such as 2-methylbutyric acid, 2-methylbutyrate, alkylpyrroles, and benzoic acid, which were important aroma components or flavor additives. This provided a theoretical reference for the application of pyrrole ester in cigarette and heat-processed food flavoring.

Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes

The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid access to O-vinyl oximes. The regioselectivity of pyrrole formation can be controlled by either the identity of the α-substituent or through the addition of an amine base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways are proposed. Conditions are provided for selecting either the [3,3] rearrangement or the [1,3] rearrangement product with β-ester O-allyl oxime substrates.

Catalytic asymmetric hydrogenation of 2,3,5-trisubstituted pyrroles

Catalytic asymmetric hydrogenation of N-Boc-protected pyrroles proceeded with high enantioselectivity by using a ruthenium catalyst modified with a trans-chelating chiral bisphosphine PhTRAP. The ruthenium catalyst prepared from Ru(η3-methallyl

Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines

The palladium-catalyzed oxidation of hydroxy-enamines, which were obtained by the condensation of β-aminoalcohols and carbonyl compounds, proceeded to give the corresponding polysubstituted pyrroles and 4,5,6,7-tetrahydroindoles in good yields. The treatment of o-(2-hydroxyethyl)aniline with the palladium catalyst also gave indole in 78% yield.