4391-98-4

Usage

Derivation

Derived from pyrrole, a five-membered aromatic heterocyclic organic compound

Use

Building block for the synthesis of various biologically active compounds in the pharmaceutical industry

Potential properties

Anti-inflammatory and anti-cancer properties

Physical properties

Colorless liquid, fruity odor, soluble in organic solvents

Safety

Handle with care and follow proper safety protocols in laboratory settings.

Upstream product

• 488-92-6 3-ethyl-4-methyl-1H-pyrrole 
• 53365-89-2 5-Ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxylic acid 
• 7467-77-8 diethyl 3-ethyl-4-methylpyrrole-2,5-dicarboxylate 
• 57745-28-5 Ethyl 4-ethyl-5-iodo-3-methylpyrrole-2-carboxylate 
• 2999-46-4 Ethyl isocyanoacetate 
• 89896-01-5 3-nitropentan-2-ol acetate 
• 5447-99-4 3-nitro-pentan-2-ol 
• 97336-18-0 4-Ethyl-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 2199-47-5 ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate 
• 1540-34-7 3-ethyl-2,4-pentanedione 

Downstream Products

• 856119-30-7 5-acetyl-4-ethyl-3-methyl-pyrrole-2-carboxylic acid ethyl ester 
• 23466-29-7 4-ethyl-3-methyl-pyrrole-2-carboxylic acid 
• 25553-59-7 2,5-bis(5-carboxy-3-ethyl-4-methyl-2-pyrrolylmethyl)furan 
• 190331-83-0 Diethyl 3,7-diethyl-2,8-dimethyl-5-phenyldihydrodipyrrin-1,9-dicarboxylate 
• 126380-11-8 ms-(4''-methoxyphenyl)-5,5'-dicarbethoxy-4,4'-dimethyl-3,3'-diethyldipyrrolylmethane 
• 102393-34-0 C₅₈H₇₀N₈O₄ 
• 102393-35-1 1,4-bis<5-<2-<(5-ethoxycarbonyl-3-ethyl-4-methylpyrrol-2-yl)methyl>-5-(2,2-dicyanovinyl)-4-methylpyrrol-3-yl>pentyl>-2,3,5,6-tetramethylbenzene 
• 102393-36-2 C₆₄H₈₂N₈O₄ 
• 144582-06-9 1,4-Bis<4-<2-((5-ethoxycarbonyl-3-ethyl-4-methylpyrrol-2-yl)methyl)-5-(2-cyano-2-methoxycarbonylvinyl)-4-methylpyrrol-3-yl>butyl>benzene 
• 51089-83-9 benzyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate 
• 6305-93-7 [5,5'-bis(ethoxycarbonyl)-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrolyl]methane 
• 988-63-6 2-<(5'-ethoxycarbonyl-3'-ethyl-4'-methylpyrrole-2-yl)methyl>-5-benzyloxycarbonyl-3-ethyl-4-methylpyrrole 
• 190331-86-3 Diethyl 3,7-diethyl-5-(4-hydroxymethylphenyl)-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate 

Relevant academic research and scientific papers

Synthesis and spectrophotometric study of acidic and complexing properties of 5,15-bis(4'-methoxyphenyl)-10,20-bis(4″-nitrophenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetraethylporphyn in acetonitrile

Abstract 5,15-Bis(4'-methoxyphenyl)-10,20-bis(4″-nitrophenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetraethylporphyne was synthesized and studied spectrophotometrically in the systems 1,8-diazabicyclo[5.4.0]undec-7-ene-acetonitrile, Zn(OAc)2-acetoni

Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines

Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2, 2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines (PGs) and tambjamines.

Artificial photosynthetic reaction centers with carotenoid antennas

Two reaction center-antenna models based on a purpurin macrocycle linked to a C60 and to a carotenoid polyene have been synthesized. In these systems the C60 moiety is the primary electron acceptor, the purpurin is the primary electr

An improved coupling procedure for the Barton-Zard pyrrole synthesis

An improved final step in the Barton-Zard pyrrole synthesis uses inexpensive potassium carbonate as base in the coupling-cyclization reaction of vic-nitro-acetates with isocyanides. In this modification the isolated yields of synthetically useful 2-carboalkoxypyrroles (1a,b and 3) and 2-(p-toluenesulfonyl)pyrroles (2a,b) consistently rise to the 78-89% range. Conversion of 2a to 5-(p-toluenesulfonyl)-2-pyrrolinone 4 is conveniently and directly achieved by reaction with 30% hydrogen peroxide in acetic acid, thus circumventing the commonly used two step procedure involving bromination followed by solvolysis.

Deiodination of 5-iodopyrrole-2-carboxylates using sodium formate catalyzed by palladium complexes: Preparation of 5-unsubstituted pyrrole-2-carboxylates

5-Iodopyrrole-2-carboxylates are deiodinated with sodium formate in the presence of a catalytic amount of either PdCl2(Ph3P)2 or Pd(Ph3P)4 to give the corresponding 5-unsubstituted pyrrole-2-carboxyla

A new convergent method for porphyrin synthesis based on a '3 + 1' condensation

A new methodology based on the '3 + 1' acid-catalytic condensation of tripyrranes and pyrrole-2,5-dicarbaldehyde has been used, for the first time, for the synthesis of two types of porphyrins: vic-dipropionic ester porphyrins 30 and 31 including an analo

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.

An Improved Approach to 5'-Unsubstituted 5-Formyldipyrromethanes

A general synthesis of 5'-unsubstituted 5-formylpyrromethanes, precursors to centrosymmetric porphyrins, is described.Cyanovinyl groups are used to protect the aldehydes and stabilize the dipyrromethanes. 5-(Chloromethyl)-2-(2,2-dicyanovinyl)pyrroles were condensed with 5-unsubstituted pyrrole-2-carboxylate ethyl esters in warm glacial acetic acid to give a series of 5'-(ethoxycarbonyl)-5-(2,2-dicyanovinyl)-2,2'-dipyrromethanes in high yield.Aqueous alkali was used to deprotect the dicyanovinyl substituent to regenerate the aldehyde and saponify the ethyl ester in a single step.The acid group was subsequently decarboxylated thermally to give the 5'-unsubstituted 5-formyl-2,2'-dipyrromethane.An alternative route was also designed by substitution of a benzyl for an ethyl ester.Hydrogenolysis released the carboxylic acid without affecting the cyanovinyl group, and the subsequent decarboxylation in neat trifluoroacetic acid accurred without rearrangement.Deprotection using aqueous alkali produced crystalline 5'-unsubstituted 5-formyldipyrromethane.The complete lack of rearrangement during the synthesis and manipulation of the dipyrromethanes was confirmed by 13C NMR spectroscopy.