2199-47-5

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-ETHYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE is used as a reagent in the synthesis of diacetylenic bilirubin, a compound with potential pharmaceutical applications. Its role in the synthesis process is crucial for the production of ETHYL 4-ETHYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE, which may have therapeutic benefits in various medical conditions.
Used in Chemical Research:
In addition to its applications in the pharmaceutical industry, ETHYL 4-ETHYL-3,5-DIMETHYL-1H-PYRROLE-2-CARBOXYLATE is also utilized in chemical research for the development of new compounds and materials. Its unique structure and reactivity make it a valuable tool for exploring novel chemical reactions and syntheses.

InChI:InChI=1/C11H17NO2/c1-5-9-7(3)10(12-8(9)4)11(13)14-6-2/h12H,5-6H2,1-4H3

Upstream product

• 52649-01-1 4-(2-bromo-vinyl)-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester 
• 6829-41-0 diethyl oximinomalonate 
• 1540-34-7 3-ethyl-2,4-pentanedione 
• 25894-11-5 ethyl 3,5-dimethyl-4-vinyl-1H-pyrrole-2-carboxylate 
• 315663-65-1 Ethyl 4-(2-chloroacetyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 2199-44-2 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole 
• 52649-02-2 5-ethoxycarbonyl-2,4-dimethylpyrrole-3-acrylic acid 
• 123-54-6 acetylacetone 
• 5408-04-8 ethyl 2-hydroxyimino-3-oxobutanoate 
• 141-97-9 ethyl acetoacetate 
• 4391-98-4 ethyl 4-ethyl-3-methylpyrrole-2-carboxylate 
• 101116-14-7 (4-acetyl-2-ethoxycarbonyl-5-methyl-pyrrol-3-yl)-acetic acid ethyl ester 
• 109394-38-9 (2-ethoxycarbonyl-4-ethyl-5-methyl-pyrrol-3-yl)-acetic acid ethyl ester 
• 6829-40-9 aminomalonic acid diethyl ester 

Downstream Products

• 517-22-6 2,4-dimethyl-3-ethyl-pyrrole 
• 6305-93-7 [5,5'-bis(ethoxycarbonyl)-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrolyl]methane 
• 6250-80-2 4-ethyl-3,5-dimethylpyrrole-2-carbaldehyde 
• 100619-73-6 ethyl 5-acetoxymethyl-4-ethyl-3-methylpyrrole-2-carboxylate 
• 881900-81-8 5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-1,9-dicarboxydipyrromethane 
• 881900-80-7 1,9-dicarbobenzyloxy-5-(4-carbomethoxyphenyl)-3,7-diethyl-2,8-dimethyl-dipyrromethane 
• 4391-98-4 ethyl 4-ethyl-3-methylpyrrole-2-carboxylate 
• 51089-83-9 benzyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate 
• 763885-46-7 C₁₅H₂₂N₂ 
• 580-47-2 etioporphyrin-IV 
• 26608-34-4 Etioporphyrin III 
• 97336-22-6 5-(benzyloxycarbonyl)-5'-(2,2-dicyanovinyl)-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrromethane 
• 97336-24-8 5-(benzyloxycarbonyl)-5'-<2-cyano-2-(methoxycarbonyl)vinyl>-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrromethane 

Relevant academic research and scientific papers

Preparation, spectral and thermal properties of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes with iodosubstituted 2,2′-dipyrrolylmethene

Complexes [ML2] of cobalt(II), nickel(II), copper(II), zinc(II), and cadmium(II) with asymmetrically substituted (E)-3-ethyl-5-[(4-iodo-3,5- dimethyl-2H-pyrrol-2-ylidene)methyl]-2,4-dimethyl-1H-pyrrole (HL) have been prepared and characterized for the first time. The spectral properties, stability in solutions and in the solid phase at elevated temperature of the complexes have been studied. The effects of complexing metal ion and the reaction medium on the spectral luminescent properties (absorptivity, quantum yield, fluorescence lifetime, and the radiation constant) and on thermal destruction of the [ML2] complexes have been discussed.

Synthesis and spectral properties of new 3,3'-bis(dipyrrolylmethene) with acetylene spacer

Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L·2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, 1H NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with-CH2-spacer. Pleiades Publishing, Ltd., 2010.

Syntheses of per-15N labeled etioporphyrins I-IV and a related tetrahydrobenzoporphyrin for applications in organic geochemistry and vibrational spectroscopy

Nitrogen-15 labeled pyrroles have been prepared from commercially available 15N glycine or sodium nitrite using the Barton-Zard, Knorr, and Kleinspehn approaches. These pyrroles were used as intermediates in the synthesis of per-15N labeled porphyrins needed for the analysis and assignment of vibrational spectra for sedimentary porphyrins. Etioporphyrin-I was prepared via pyrromethene intermediates, while etioporphyrins II-V and a related tetrahydrobenzoporphyrin were synthesized via stepwise routes involving the copper(II) mediated cyclization of a,c-biladienes as the key step. Detailed analyses of both the proton and carbon-13 NMR spectra provide nitrogen-15 coupling constants for these important structures.

Reduction of acyl pyrrole esters by zinc-hydrochloric acid

The pyrryl alkyl ketone and acetylpyrrole esters were reduced to corresponding alkylpyrrole esters by zinc-hydrochloric acid in alcohol in high yields (> 90%).

Thermochemistry of substituted pyrroles

The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K.The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.

SYNTHESIS OF MESO-DIPHENYLOCTAALKYLPORPHYRINS

Procedures were developed for the synthesis of phenyl(β-tetraalkyldipyrrolyl)methanes.On their basis 3,7,13,17-tetramethyl-2,8,12,18-tetrabutyl-5,15-diphenylporphyrin, 2,8,12,18-tetramethyl-3,7,13,17-tetrabutyl-5,15-diphenylporphyrin, 2,8,12,18-tetramethyl-3,7,13,17-tetraethyl-5,15-diphenylporphyrin, and derivatives of the last two porphyrins containing electron-donating (2-CH3O, 3-CH3O, 4-CH3O) and electron-withdrawing (3-NO2, 4-NO2) substituents in the benzene rings were obtained.

ELECTROPHILIC HETEROAROMATIC SUBSTITUTIONS. X. UNEXPECTED RESULTS IN THE α-SIDE-CHAIN CHLORINATION OF A SERIES OF ETHYL 3,4,5-TRIALKYLPYRROLE-2-CARBOXYLATES

The reaction of a series of 3,4,5-trialkyl-substituted ethyl pyrrole-2-carboxylates with an excess of sulphuryl chloride followed by solvolysis has been investigated in several solvents and under different experimental conditions.In all cases, beside the expected α-side-chain substituted product, substantial amounts of derivatives functionalised also in a β-side chain have been isolated and identified.The process turned out to be electrophilic in nature and to involve allylic migration of the halogen from the α-sigma adduct to the adjacent β-side chain.Virtually identical results have been obtained when elemental chlorine was used.

Pyrrole Chemistry. An Improved Synthesis of Ethyl Pyrrole-2-carboxylate Esters from Diethyl Aminomalonate

Ethyl pyrrole-2-carboxylates, versatile precursors for the total synthesis of both synthetic model and naturally occurring tetrapyrroles and porphyrins, can be prepared in greatly improved yields by the addition of 1,3-diketones and preformed diethyl aminomalonate to boiling glacial acetic acid.The method is suitable for both small- and large-scale synthesis and has proved far more reliable than the original in situ dissolving zinc reduction of diethyl oximinomalonate discovered by Kleinspehn.Yields range from 60-70percent for the dominant product isomer from unsymmetrical diketones to 75-90percent for the single product derived from symmetrical diketones.Seventeen examples of alkyl-substituted ethyl pyrrole-2-carboxylates are provided.Improved procedures are given for the preparation of the required precursors.