1551-16-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-ETHYL-1H-PYRROLE is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows it to be a versatile building block for the development of new drugs and pesticides.
Used in Fragrance Industry:
3-ETHYL-1H-PYRROLE is used as a fragrance ingredient in perfumes and flavoring agents due to its characteristic odor. Its ability to impart specific scents makes it a valuable component in the creation of various fragrances.
Used in Materials Science:
3-ETHYL-1H-PYRROLE has potential applications in the field of materials science, particularly in the development of organic semiconductors for electronics and optoelectronic devices. Its properties contribute to the advancement of these technologies.
Used in Natural Products:
3-ETHYL-1H-PYRROLE is found in some natural products and contributes to the scent of certain flowers. Its presence in these natural sources highlights its potential for use in the development of natural-based fragrances and other applications.

InChI:InChI=1/C6H9N/c1-2-6-3-4-7-5-6/h3-5,7H,2H2,1H3

Upstream product

• 1072-82-8 3-acetylpyrrole 
• 109-97-7 pyrrole 
• 14936-94-8 ethyl cation 
• 52866-26-9 ((E)-Buta-1,3-dienyl)-diethyl-amine 
• 201230-82-2 carbon monoxide 
• 71580-34-2 3-vinyl-1H-pyrrole 
• 860759-68-8 4-ethyl-5-methyl-pyrrole-2,3-dicarboxylic acid-3-ethyl ester 
• 106058-85-9 1-(1-tosyl-1H-pyrrol-3-yl)ethan-1-one 
• 97188-23-3 3-ethyl-1-phenylsulfonylpyrrole 
• 117270-78-7 N-(triisopropylsilyl)-3-ethylpyrrole 
• 81453-98-7 3-acetyl-1-(phenylsulfonyl)pyrrole 
• 66414-04-8 diethyl 3-ethyl-5-methylpyrrole-2,4-carboxylate 
• 1260827-11-9 methyl 4-ethyl-1H-pyrrole-3-carboxylate 
• 111468-98-5 2,4,5-triiodo-3-acetylpyrrole 

Downstream Products

• 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 
• 355114-76-0 3-ethyl-1-(2-methyl-2-propenyl)pyrrole 
• 63009-16-5 2-ethyltetramethylenediamine 
• 97188-23-3 3-ethyl-1-phenylsulfonylpyrrole 
• 111495-43-3 2-ethyl-1,4-bis<(benzyloxycarbonyl)amino>butane 
• 97188-34-6 2-acetyl-3-ethyl-1-(phenylsulfonyl)pyrrole 
• 97188-35-7 4-acetyl-3-ethyl-1-(phenylsulfonyl)pyrrole 
• 97188-36-8 5-acetyl-3-ethyl-1-(phenylsulfonyl)pyrrole 
• 97188-37-9 2-acetyl-3-ethylpyrrole 
• 97188-45-9 2-acetyl-4-ethylpyrrole 

Relevant academic research and scientific papers

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.

Metal-Free Directed C?H Borylation of Pyrroles

Robust strategies to enable the rapid construction of complex organoboronates in selective, practical, low-cost, and environmentally friendly modes remain conspicuously underdeveloped. Here, we develop a general strategy for the site-selective C?H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site-selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2-borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations, enabling a step-economic process to access drugs such as Lipitor. DFT calculations (wB97X-D) demonstrate the preferred positional selectivity of this reaction.

Synthesis process method of 3-substituted-1H-pyrrole

The invention provides a synthetic process method of a 3-substituted-1H-pyrrole compound. The process method comprises the following steps: by taking diethylamine hydrochloride and glycine ethyl esterhydrochloride as initial raw materials, respectively carrying out Mannich reaction and sulfamide reaction, and carrying out cyclization reaction, dehydration thinning reaction, aromatization reactionand hydrolysis decarboxylation reaction to obtain a 3-substituted-1H-pyrrole compound. According to the synthesis process method of the 3-substituted-1H-pyrrole compound, the whole synthesis route isgood in step repeatability, mild in operation condition and high in safety, and large-scale production and industrial popularization are facilitated; post-treatment energy consumption is low, a largeamount of toxic wastewater is not generated, no pollution is caused to the environment, the production safety level and the production cost are reduced, application of green and environment-friendlyindustrial production is facilitated, and wide application prospects are achieved.

A highly efficient gas-dominated and water-resistant flame retardant for non-charring polypropylene

Traditional phosphorus-nitrogen (P-N) flame-retardant systems for polypropylene (PP) always act through joint action of the gaseous phase and condensed phase, and are accompanied with a decrease of the thermal stability and water resistance. In this work, a novel mono-component and gas-dominated flame retardant, named DPPIP, was prepared through an amidation reaction of diphenylphosphinyl chloride and piperazine, and used to flame retard PP. Experimental results confirmed that both the thermal stability and water resistance of PP/DPPIP were improved. The initial thermal decomposition temperature of PP/25 wt% DPPIP at 5 wt% weight loss was 287.5 °C under air atmosphere, which is higher than that of neat PP (266.1 °C). Besides, a water-resistance test verified that PP/25 wt% DPPIP had a weight loss of only about 0.52 wt%. More importantly, the flame retardant ability of PP/25 wt% DPPIP had been greatly improved, passing the V-0 rating (UL-94). Furthermore, after the water-resistance test, the LOI value of PP/25 wt% DPPIP exhibited nearly no difference and still passed the UL-94 V-0 rating. A cone calorimeter (CC) result indicated that DPPIP had a positive effect on inhibiting heat release of PP during combustion. All of these combustion tests displayed that there was no char left. The flame retardant mechanism of DPPIP was investigated with py-GC/MS and TG-FTIR. The results illustrated that the gaseous phase resulting from the thermal decomposition of DPPIP played the leading role in the self-extinguishing behavior of PP/DPPIP, which consisted of a large amount of inflammable gaseous products such as piperazine and its derivatives, and phosphorus-containing structures.

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.

Development of two processes for the synthesis of bridged azabicyclic systems: Intermolecular radical addition-homoallylic rearrangements leading to 2-azanorborn-5-enes and neophyl-type radical rearrangements to 2-azabenzonorbornanes

Radical thiol additions to 7-azanorbornadienes give 7-thio-substituted 2-azanorbornenes and Barton deoxygenations of 7-azabenzonorbornanols give 2-azabenzonorbornanes. The processes both involve novel nitrogen-directed radical rearrangements. The kinetics and mechanisms of the reactions are also discussed.

2-azabenzonorbornanes from 7-azabenzonorbornanols by a nitrogen-directed neophyl-type radical rearrangement

(equation presented) Barton deoxygenation of 7-azabenzonorbornanols leads to a synthetically useful neophyl-like rearrangement to give 2-azabenzonorbornane derivatives in 64-90% yields.

Influence of the reaction temperature on the regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles

The influence of the temperature on the regioselectivity in the hydroformylation of the vinylpyrrole isomers and of the corresponding N-tosylated substrates has been investigated in the range 20-100°C, in the presence of Rh4(CO)12. At all the temperatures the branched aldehyde was prevailing with respect to the linear isomer for all the substrates ( α-regioselectivity). With increasing temperature, an increase of the linear aldehyde was observed to a different extent in dependence on the substrate nature. 2H NMR investigation of the crude reaction mixture recovered from deuterioformylation of 3-vinylpyrrole at partial substrate conversion points out that the observed depression of the α-regioselectivity with increasing temperature must be connected to a β-hydride elimination process occurring for the branched alkyl-rhodium intermediates but not for the linear ones.

High α-regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles

The Rh4(CO)12-catalyzed hydroformylation at low temperature (40°C) of the 1-, 2- and 3-vinylpyrrole gives the corresponding branched aldehydes 2-(1-pyrrolyl)propanal, 2-(2-pyrrolyl)propanal and 2-(3-pyrrolyl)propanal with high α-regioselectivity.