1072-82-8

Usage

Uses

Used in Research and Development:
3-Acetylpyrrole is used as a research reagent for organic synthesis and other chemical and pharmaceutical processes. Its unique structure and properties make it a valuable compound for studying various chemical reactions and developing new synthetic methods.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Acetylpyrrole is used as an intermediate in the synthesis of various drugs and drug candidates. Its versatile chemical properties allow it to be a key component in the development of new medications with potential therapeutic applications.
Used in Chemical Industry:
3-Acetylpyrrole is also utilized in the chemical industry for the production of various specialty chemicals and materials. Its unique structure and reactivity make it a valuable building block for the synthesis of complex organic molecules with specific properties and functions.

Synthesis Reference(s)

Canadian Journal of Chemistry, 58, p. 2527, 1980 DOI: 10.1139/v80-404Synthetic Communications, 17, p. 401, 1987 DOI: 10.1080/00397918708063917Tetrahedron Letters, 22, p. 4901, 1981 DOI: 10.1016/S0040-4039(01)92377-9

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

Upstream product

• 109-97-7 pyrrole 
• 593-53-3 Methyl fluoride 
• 201230-82-2 carbon monoxide 
• 21872-75-3 diethoxy(methyl)carbenium tetrafluoroborate 
• 111468-98-5 2,4,5-triiodo-3-acetylpyrrole 
• 16168-93-7 4-acetyl-2-pyrrolecarboxylic acid 
• 108-24-7 acetic anhydride 
• 106058-85-9 1-(1-tosyl-1H-pyrrol-3-yl)ethan-1-one 
• 87630-35-1 N-triisopropylsilylpyrrole 
• 119647-69-7 ethyl 4-acetylpyrrole-2-carboxylate 
• 2199-43-1 ethyl 1H-pyrrole-2-carboxylate 
• 72652-34-7 1-(4-acetyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one 
• 405219-06-9 1-(1-diethoxymethyl-1H-pyrrole-3-yl)ethanone 
• 64-19-7 acetic acid 

Downstream Products

• 111495-43-3 2-ethyl-1,4-bis<(benzyloxycarbonyl)amino>butane 
• 63009-16-5 2-ethyltetramethylenediamine 
• 134161-62-9 3-thioacetylpyrrole 
• 1072-83-9 2-Acetylpyrrole 
• 1551-16-2 3-ethyl-1H-pyrrole 
• 63547-61-5 1,1'-(1H-pyrrole-2,4-diyl)bis(ethan-1-one) 
• 122450-29-7 1-chlorobenzyl-3-acetylpyrrole 
• 147088-96-8 1-(5-benzoyl-1H-pyrrol-3-yl)ethanone 
• 128942-91-6 1-Benzyl-3-acetylpyrrole 
• 128942-90-5 1-Ethyl-3-acetylpyrrole 
• 219910-55-1 3-acetyl-1-vinylpyrrole 
• 1326240-86-1 rac-8-ethyl-1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine 
• 1326240-87-2 rac-7-ethyl-1-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine 

Relevant academic research and scientific papers

A SIMPLE AND EFFICIENT ROUTE TO β-SUBSTITUTED PYRROLES

N-Phenylsulfonylpyrrole undergoes Friedel-Crafts acylation exclusively at the β-position of the pyrrole ring, thus allowing a simple and efficient synthesis of β-acylated pyrroles.

Friedel-Crafts acylation of pyrrole over ultrasonic-assisted phosphoric acid-modified Hβ zeolite

Friedel-Crafts acylation of pyrrole with acetic anhydride was studied over different zeolites and an ultrasonic-assisted phosphoric acid-modified Hβ (P-Hβ-US) zeolite was found to have the best catalytic performance among all the zeolites examined. The conversion of acetic anhydride reached 98.8% and the selectivity to acetylpyrroles was 97.0% under the optimized conditions. The high activity of the P-Hβ-US zeolite is attributed to the increase of weak acid sites, caused by the synergistic effect between the phosphoric acid modification and ultrasound. Moreover, the carbonaceous deposits, mainly due to the adsorption of reactants and products, on the surface acid sites and the blockage of the pores is believed to be the reason for the deactivation of the reused P-Hβ-US zeolite, confirmed from the Brunauer-Emmett-Teller (BET) method, scanning electron microscopy, and X-ray photoelectron spectroscopy. Furthermore, the catalyst activity can be recovered effectively by a subsequent calcination. Springer Science+Business Media B.V. 2011.

Synthesis of industrially important aromatic and heterocyclic ketones using hierarchical ZSM-5 and Beta zeolites

Hierarchical ZSM-5 and Beta zeolites were investigated in the synthesis of wide range of industrially important aromatic/heterocyclic ketones by Friedel-Crafts acylation and benzoylation reactions. For comparative study, conventional ZSM-5 and Beta, and amorphous mesoporous Al-MCM-41 were investigated. Hierarchical zeolites were prepared by multi-ammonium structure directing agents whereas conventional zeolites were prepared by mono-ammonium structure directing agents. Among the catalysts investigated in this study, hierarchical Beta exhibited the highest reactant conversion in the acylation and benzoylation reactions. In this study, the systematic assessment of the catalytic activity of acid catalysts for wide range of aromatic and heterocyclic compounds is shown under one umbrella. To the best of our knowledge, these reactions over hierarchical zeolites (ZSM-5 and Beta) are reported here for the first time. Structure activity relationship is explained based on the physico-chemical properties, molecular size, reactivity of reactants, and reaction mechanism. Catalysts can be easily recovered and reused with negligible loss in the catalytic activity.

Pyrrole Hemithioindigo Antimitotics with Near-Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single-Cell Precision**

We report the first cellular application of the emerging near-quantitative photoswitch pyrrole hemithioindigo, by rationally designing photopharmaceutical PHTub inhibitors of the cytoskeletal protein tubulin. PHTubs allow simultaneous visible-light imaging and photoswitching in live cells, delivering cell-precise photomodulation of microtubule dynamics, and photocontrol over cell cycle progression and cell death. This is the first acute use of a hemithioindigo photopharmaceutical for high-spatiotemporal-resolution biological control in live cells. It additionally demonstrates the utility of near-quantitative photoswitches, by enabling a dark-active design to overcome residual background activity during cellular photopatterning. This work opens up new horizons for high-precision microtubule research using PHTubs and shows the cellular applicability of pyrrole hemithioindigo as a valuable scaffold for photocontrol of a range of other biological targets.

Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines

Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.

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.

Direct synthesis of chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines via a catalytic asymmetric intramolecular aza-Friedel-Crafts reaction

The direct asymmetric intramolecular aza-Friedel-Crafts reaction of N-aminoethylpyrroles with aldehydes catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines with high yields and high enantioselectivities. This strategy has been shown to be quite general toward various aldehydes and pyrrole derivatives.

Amberlyst-15 catalyzed acetylation of heteroaromatics with acetic anhydride under solvent free conditions

Amberlyst-15 has been found to be an efficient reusable heterogeneous catalyst for acetylation of indole, 2-methylindole and pyrrole with acetic anhydride under solvent free conditions.

Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions

Stable and non-hygroscopic aluminum dodecatungstophosphate (AlPW 12O40), which is prepared easily from cheap and commercially available compounds was found to be an effective catalyst for Friedel-Crafts acylation reactions using carboxylic acids, acetic anhydride and benzoyl chloride in the absence of solvent under mild reaction conditions.

Aromatic heterocycle compounds having HIV integrase inhibiting activities

A compound of the formula (I): wherein X is hydroxy, protected hydroxy or optionally substituted amino; Y is —COORAwherein RAis hydrogen or ester residue, —CONRBRCwherein RBand RCeach is independently hydrogen or amide residue, optionally substituted aryl or optionally substituted heteroaryl; and A1is optionally substituted heteroaryl; provided that a compound wherein Y and/or A1is optionally substituted indol-3-yl is excluded, a tautomer, a prodrug, a pharmaceutically acceptable salt or a hydrate thereof has an inhibitory activity against an integrase.