23351-07-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-(1H-Pyrrol-1-yl)benzonitrile is used as a synthetic intermediate for the development of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a diverse range of compounds with potential therapeutic and pesticidal properties, contributing to the advancement of healthcare and agriculture.
Used in Organic Synthesis:
As a key component in organic synthesis, 4-(1H-Pyrrol-1-yl)benzonitrile is utilized for the production of a wide array of organic compounds. Its presence in the molecular structure facilitates the formation of new chemical entities, expanding the scope of chemical research and innovation.
Used in Electronic Device Manufacturing:
4-(1H-Pyrrol-1-yl)benzonitrile is used as a precursor in the development of organic light-emitting diodes (OLEDs) and other electronic devices. Its electronic properties make it a valuable component in the design and fabrication of advanced electronic components, driving progress in the field of electronics and optoelectronics.
Used in Chemical Research:
In the realm of chemical research, 4-(1H-Pyrrol-1-yl)benzonitrile serves as a model compound for studying the properties and reactions of benzene derivatives with pyrrole rings and nitrile groups. Its use in research helps to deepen the understanding of chemical behavior and paves the way for the discovery of new synthetic pathways and applications.

InChI:InChI=1/C11H8N2/c12-9-10-3-5-11(6-4-10)13-7-1-2-8-13/h1-8H

Upstream product

• 109-97-7 pyrrole 
• 623-00-7 4-bromobenzenecarbonitrile 
• 143-33-9 sodium cyanide 
• 92636-36-7 1-(4-iodophenyl)pyrrole 
• 623-03-0 4-Cyanochlorobenzene 
• 5044-38-2 1-(4-chlorophenyl)-1H-pyrrole 
• 109-74-0 propyl cyanide 
• 10282-30-1 4-pyrrolidin-1-yl-benzonitrile 
• 14906-59-3 4-cyanopyridine N-oxide 
• 23351-09-9 4-(1H-pyrrol-1-yl)phenol 
• 874-90-8 4-methoxybenzonitrile 
• 119072-55-8 tert-butylisonitrile 
• 1452859-14-1 C₁₂H₉N 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 

Downstream Products

• 1210478-88-8 (C₆F₅C₆F₄)2Zn(NCC₆H₄C₄H₄N)2 
• 1443126-32-6 5-[4-(pyrrol-1-yl)phenyl]tetrazole 
• 169036-66-2 C₁₂H₈N₂O 

Relevant academic research and scientific papers

Organic dyes incorporating N-functionalized pyrrole as conjugated bridge for dye-sensitized solar cells: Convenient synthesis, additional withdrawing group on the π-bridge and the suppressed aggregation

Two new N-functionalized pyrrole-based organic dyes were designed and synthesized for dye-sensitized solar cells. In addition to the normal acceptor of cyanoacetic acid moieties, another electron-withdrawing group, pentafluorophenyl or cyanophenyl one, wa

Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis

A metal-free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature has been developed. This TEMPO-mediated electrocatalytic reaction makes full use of both anodic oxidation and cathodic reduction without metals or stoichiometric oxidants, thus showing great potential and advantages for practical synthesis. This convergent paired electrolysis method provides a straightforward and powerful means to activate C?H bonds and realize cross-coupling with cathodically generated species.

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Lactam derivatives and preparation method and application thereof

The invention relates to lactam derivatives and a preparation method and application thereof. Compared with the prior art, the invention provides lactam compounds with a novel structure. The compoundsand compositions thereof have remarkable activity in inhibition of the proliferation of cancer cells (including, but not limited to, the liver cancer cell line HepG2 and the lung cancer cell line A549), and the activity of multiple compounds is in the same order of magnitude as the activity of the commercial drug adriamycin or superior to the activity of adriamycin. The compounds of the inventioncan be prepared from N-substituted pyrrole compounds through a reaction, and the preparation method is convenient, rapid and efficient.

Phosphazene Base tBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes

The organic superbase tBu-P4 catalyzes methoxy-alkoxy exchange reactions on (hetero)arenes with alcohols. The catalytic reaction proceeded efficiently with electron-deficient methoxy(hetero)arenes as well as with a variety of alcohols, including 3-amino-1-propanol, β-citronellol, menthol, and cholesterol. An intramolecular version of this reaction furnished six- and seven-membered ring compounds.

Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A wide range of bridge-ring amines with various substituents have been synthesized in moderate to excellent yields (35-96%). Furthermore, with a catalytic amount of TsOH·H2O, these amines can be converted into the corresponding N-phenylamine derivatives easily, which are potentially useful in photosensitive dyes.

Thieme Chemistry Journals Awardees - Where Are They Now? Efficient Cross-Coupling of Secondary Amines/Azoles and Activated (Hetero)Aryl Chlorides Using an Air-Stable DPEPhos/Nickel Pre-Catalyst

Synthesis and characterization of the new air-stable pre-catalyst (DPEPhos)Ni(2-mesityl)Br (C1) is reported, along with the application of this pre-catalyst in the cross-coupling of secondary amines/azoles with activated (hetero)aryl chlorides to afford t

A carbon nitride supported copper nanoparticle composite: a heterogeneous catalyst for the N-arylation of hetero-aromatic compounds

A graphitic carbon nitride supported copper nanoparticle composite (Cu-gCN) has been found to be an active catalyst for the N-arylation of hetero-aromatic systems (pyrrole, pyrazole, and substituted indole) and benzamide molecules, with high product selectivity and good to excellent yields, using substituted aryl bromide as a coupling partner. The intercalated structure and the amine functional group of the carbon nitride prevent the aggregation of the catalytically active copper species during the reaction, and the recyclability study shows the stable performance of the catalyst without a significant loss of catalytic activity.

Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling

We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.

Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis-aromatization sequence.