43036-06-2

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-CYANOETHYL)PYRROLE is used as a synthetic intermediate for the production of 2-pyridines, which are important compounds in the development of pharmaceuticals. These 2-pyridines have potential applications in the treatment of various diseases due to their diverse biological activities.
Used in Chemical Synthesis:
N-(2-CYANOETHYL)PYRROLE is also used in the preparation of indoles and pyrroles, which are significant classes of heterocyclic compounds with a wide range of applications in the chemical, pharmaceutical, and agrochemical industries. Indoles, for instance, are found in numerous natural products and have been used as building blocks for the synthesis of various bioactive molecules, including pharmaceuticals, dyes, and pigments.

InChI:InChI=1/C7H8N2/c8-4-3-7-9-5-1-2-6-9/h1-2,5-6H,3,7H2

Upstream product

• 542-76-7 3-Chloropropionitrile 
• 16199-06-7 potassium pyrrolide 
• 109-97-7 pyrrole 
• 107-13-1 acrylonitrile 
• 34583-60-3 p-CH₃C₆H₄-O₂SO-CH₂CH₂CN 
• 31164-08-6 3-(diallylamino)propanenitrile 

Downstream Products

• 17266-64-7 1,2-dihydro-1-pyrrolizinone 
• 60794-90-3 3-pyrrol-1-yl-propylamine 
• 89059-06-3 N-(2-carboxyethyl)pyrrole 
• 15620-48-1 4,6-dimethyl-2-(2-pyrrol-1-yl-ethyl)-5,6-dihydro-4H-[1,3,4]thiadiazine 
• 6311-84-8 2-[2-(pyrrol-1-yl)ethyl]pyridine 
• 865763-00-4 (3-formyl-2-hydroxyphenyl) 3-(pyrrol-1-yl)propanoate 
• 157614-76-1 Pentafluorophenyl 3-(pyrrol-1-yl)propanoate 
• 157614-80-7 (3-Pyrrol-1-yl-propionylamino)-acetic acid pentafluorophenyl ester 
• 1226779-92-5 C₁₅H₁₄N₂ 
• 1226779-97-0 C₁₇H₁₉N₃ 
• 1226779-96-9 C₁₆H₁₆N₂O 
• 1226779-94-7 C₁₆H₁₆N₂ 
• 1242419-83-5 C₁₆H₁₇N₃ 
• 1256844-82-2 3-(2-benzoyl-1H-pyrrol-1-yl)propanenitrile 

Relevant academic research and scientific papers

Electrochemical polymerization of pyrrole containing TEMPO side chain on pt electrode and its electrochemical activity

Poly(4-(3-(pyrrol-1-yl)propionyloxy)-2,2,6,6-tetramethylpiperidin-1-yloxy) (PPy-TEMPO) electrode is prepared by electrochemical polymerization on Pt electrode in NaClO4-CH3CN solution. The electrocatalytic activity of PPy-TEMPO for benzyl alcohol in NaClO4-CH3CN solution is investigated by cyclic voltammetry and in situ FTIR. Results show that PPy-TEMPO electrode exhibits high electrocatalytic activity for benzyl alcohol oxidation in the presence of 2,6-lutidine as the base, as compared with the bare Pt electrode under the similar conditions. On the basis of in situ FTIR data, it shows that TEMPO is oxidized to its cation at the potential about 0.4 V, and benzyl alcohol is oxidized to benzaldehyde instead of benzoic acid. Further studies of preparative electrolysis experiments by constant current electrolysis are carried out to confirm the high conversion to benzaldehyde, and the results are in good agreement with those from in situ FTIR investigations.

Sensitive amperometric immunosensing using polypyrrolepropylic acid films for biomolecule immobilization

An electrochemical immunosensor was constructed using an electropolymerized pyrrolepropylic acid (PPA) film with high porosity and hydrophilicity. A high density of carboxyl groups of PPA was used to covalently attach protein probes, leading to significantly improved detection sensitivity compared with conventional entrapment methods. As a model, anti-mouse IgG was covalently immobilized or entrapped in the PPA film and used in a sandwich-type alkaline phosphatase-catatyzing amperometric immunoassay with p-aminophenyl phosphate as the substrate. With covalent binding, the detection limit for IgG in PBS buffer, pH 7.4, was 100 pg/mL with a dynamic range of 5 orders of magnitude. The covalent bonding mode in the carbonate-bicarbonate buffer, pH 9.6, further brought down the detection limit to 20 pg/mL with remarkable selectivity.

Tricyclic pyrazoles: An efficient approach to cannabinoid analogues with a tricyclic framework incorporating the pyrrole and pyrazole moieties

In this paper we report the synthesis of some new cannabinoid analogues that share with rimonabant, a potent and selective CB1 antagonist, the 2,4-dichlorophenyl and piperidin-1-yl substituents on the pyrazole and amide nitrogens, respectively. The general synthesis involves the preparation of a cyclic ketone condensed with a pyrrole, followed by Claisen condensation with diethyl oxalate; from here, an aza-annulation reaction with a substituted hydrazine followed by an amidation step complete the synthesis. Georg Thieme Verlag Stuttgart.New York.

Friedel - Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) has been shown to be an effective catalyst for the regioselective Friedel - Crafts C-acylation of pyrroles and indoles in high yields. A detailed mechanistic study implies that DBN is acting as a nucleophilic organocatalyst, with the X-ray crystal structure of a key N-acyl-amidine intermediate having been determined for the first time.

Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes

Substoichiometric loadings of DBU catalyse the efficient 1,4-addition of alcohols and non-nucleophilic amines such as pyrrole to activated alkenes; the application of this methodology in a one-pot synthesis of a natural product, and as a novel strategy for the synthesis of mono-protected 1,3-carbonyl compounds is reported.

Pyrrole synthesis using a tandem Grubbs' carbene-RuCl3 catalytic system

A straightforward pyrrole synthesis from diallylamines is developed by using a tandem catalyst system leading to ring-closing metathesis with the second generation Grubbs' catalyst (10%) followed by dehydrogenation in the presence of RuCl3 × H2O (2%).

Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.

Polypyrrole-supported graphite felt for acetylene coupling reaction in solid phase

Substrate immobilization on graphite felt for solid-phase acetylene coupling reaction was achieved by electrochemical polymerization of the substrate precursor containing a pyrrole side chain, where the amount of substrate on the electrode surface was easily controlled by the number of repeated cyclic voltammetric scannings. Couplings between terminal acetylenes and the iodobenzene-modified graphite felt electrode or aromatic iodides and the terminal acetylene-modified graphite felt electrode in the presence of palladium catalyst proceeded smoothly in satisfactory yields.

Synthesis of amino-1,2-dihydro-1-pyrrolizinones

Three isomers of amino-1,2-dihydro-1-pyrrolizinone 5 were prepared by reductions of the corresponding nitro compounds 4, which were prepared by nitration of 1,2-dihydro-1-pyrrolizinone 3 with HNO3/(CH 3CO)2O at 0°.

New approach to rapid generation and screening of diverse catalytic materials on electrode surfaces

This paper describes a general approach to rapid generation and screening of catalytic materials on electrode surfaces. The properties of the corresponding polymers, including catalytic performance, can be modulated by varying the monomer feed ratios, monomer concentrations, and applied polymerization potential. Thus, the generation of the polymeric TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) catalysts was performed by electrochemical copolymerization of 2,2'-bithiophene with the TEMPO catalyst precursors containing pyrrole side chains. A library of catalyst films was obtained over a wide range of bithiophene/pyrrole ratios upon repeated scanning of the applied potential from +0.5 to +1.4 V (vs Ag/AgCl). The resulting catalyst films were utilized in both chemical and electrochemical oxidation of primary alcohols to aldehydes.