32111-34-5

Basic information

• Product Name: 4-(2-PYRIDYL)BENZONITRILE
• Synonyms: AKOS BAR-0494;4-(2-PYRIDYL)BENZONITRILE;4-(2-PYRIDINYL)BENZONITRILE;4-(2-PYRIDYL)BENZONITRIL;2-(4-Cyanophenyl)pyridine;4-(pyridin-2-yl)benzonitrile
• CAS NO: 32111-34-5
• Molecular Formula: C₁₂H₈N₂
• Molecular Weight: 180.21
• EINECS: 250-921-9
• Product Categories: pharmacetical
• Mol File: 32111-34-5.mol

Chemical Properties

• Melting Point: 91-92 °C
• Boiling Point: 346.5 °C at 760 mmHg
• Flash Point: 121 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 5.74E-05mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• PKA: 3.79±0.25(Predicted)
• CAS DataBase Reference: 4-(2-PYRIDYL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-PYRIDYL)BENZONITRILE(32111-34-5)
• EPA Substance Registry System: 4-(2-PYRIDYL)BENZONITRILE(32111-34-5)

Safety Data

• Hazardous Substances Data: 32111-34-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-(2-Pyridyl)benzonitrile is used as a building block for the synthesis of various organic compounds, contributing to the development of new chemical entities with potential applications in different fields.
Used in Pharmaceutical Research:
PBND is utilized as a key intermediate in the pharmaceutical industry, aiding in the creation of novel drug candidates and enhancing the therapeutic potential of existing medications.
Used in Agrochemical Production:
4-(2-Pyridyl)benzonitrile is used as a raw material in the production of agrochemicals, playing a crucial role in the development of effective and safe crop protection agents.
Used in Dye Manufacturing:
PBND serves as a precursor in the manufacturing of dyes, contributing to the coloration and performance of various dye products.
Used as a Reagent in Organic Compound Preparation:
4-(2-Pyridyl)benzonitrile is employed as a reagent in the preparation of a wide range of organic compounds, facilitating the synthesis of complex molecules and expanding the scope of chemical research.
Used in Catalysis and Materials Science:
PBND is known for its ability to form coordination complexes with transition metals, which has potential applications in catalysis and materials science, contributing to the advancement of these fields.
Used in Anticancer Research:
4-(2-Pyridyl)benzonitrile has been studied for its potential biological activities, including its use as an anticancer agent, indicating its potential in the development of new cancer treatments.

InChI:InChI=1/C12H8N2/c13-9-10-4-6-11(7-5-10)12-3-1-2-8-14-12/h1-8H

Upstream product

• 65007-00-3 pyridin-2-yl trifluoromethanesulfonate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 109-04-6 2-bromo-pyridine 
• 18471-73-3 4-(pyridin-2-yl)aniline 
• 623-03-0 4-Cyanochlorobenzene 
• 81745-83-7 pyridin-2-ylzinc(ll) bromide 
• 126747-14-6 4-cyanophenylboronic acid 
• 873-74-5 4-Aminobenzonitrile 
• 1104637-58-2 6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione 
• 109-09-1 2-chloropyridine 
• 142-08-5 2-hydroxypyridin 
• 110-86-1 pyridine 
• 3058-39-7 4-iodobenzonitrile 
• 25108-36-5 potassium picolinate 

Downstream Products

• 4385-62-0 4-(pyridin-2-yl)benzoic acid 
• 294647-97-5 1-[4-(pyridin-2-yl)phenyl]methanamine 
• 98061-21-3 4-pyridin-2-yl-benzoic acid methyl ester 
• 820231-70-7 4-(pyridin-2-yl)isonaphthalonitrile 
• 1220099-88-6 5-cyano-2-(pyridin-2-yl)phenyl benzoate 
• 1335209-96-5 2-(4'-methoxy-5-cyanobiphenyl-2-yl)pyridine 
• 1335209-95-4 6-(pyridin-2-yl)-[1,1'-biphenyl]-3-carbonitrile 
• 1345883-55-7 C₁₂H₇N₃O₂ 
• 1393520-18-7 5-cyano-N-phenyl-2-(pyridin-2-yl)benzamide 
• 1449414-88-3 3-benzoyl-4-(pyridin-2-yl)benzonitrile 
• 1449414-93-0 C₂₀H₁₄N₂O 
• 1498234-59-5 methyl 4-((5-cyano-2-(pyridin-2-yl)phenyl)(hydroxy)amino)benzoate 
• 1584673-12-0 3-(phenylthio)-4-(pyridin-2-yl)benzonitrile 
• 1008-89-5 2-phenylpyridine 

Relevant articles and documents

Iridium-based lab-on-a-molecule for Hg2+ and ClO- with two distinct light-up emissions

The nonemissive iridium complex 2 is a lab-on-a-molecule for the highly selective detection of Hg2+ and ClO- among 33 analytes using its oxime residues as reactive units. At pH 5, chemodosimeter 2 responds to Hg2+ by dehydration, whereas at pH 8, it is oxidized by ClO -, resulting in 450- and 235-fold emission increases, respectively, at two distinct wavelengths.

Synthesis method of 4-(2-pyridyl) cyanophenyl

The invention relates to a synthesis method of 4-(2-pyridyl) cyanophenyl, and belongs to the technical field of synthesis of drug intermediates. In order to solve the problems of heavy pollution and low yield in the prior art, the invention provides a synthesis method of 4-(2-pyridyl) cyanophenyl. The method is characterized by comprising the steps of in the presence of inorganic base, reacting 2-halogenated pyridine with p-cyanophenylboronic acid in an ether solvent under the catalysis of ferric acetylacetonate to obtain the corresponding product 4-(2-pyridyl) cyanophenyl. The method has the advantages of high product yield and purity, the product yield reaches 80% or above, the problem of poor reaction selectivity due to the adoption of a Grignard reagent or a lithium reagent can be effectively avoided, and the method is environment-friendly.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone

A novel nickel-catalyzed reductive cross-coupling between aryl iodides and difluoromethyl 2-pyridyl sulfone (2-PySO2CF2H) enables C(sp2)-C(sp2) bond formation through selective C(sp2)-S bond cleavage, which demonstrates the new reactivity of 2-PySO2CF2H reagent. This method employs readily available nickel catalyst and sulfones as cross-electrophile coupling partners, providing facile access to biaryls under mild reaction conditions without pregeneration of arylmetal reagents.

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction

The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.

A scalable synthesis of biaryl unit of the HIV protease inhibitor atazanavir

Atazanavir is one of the most prescribed HIV-1 protease inhibitors approved by the FDA. It was the first protease inhibitor approved for once-a-day dosing to treat AIDS due to good oral bioa-vailability and favorable pharmacokinetic profile. This research aims to develop a new synthetic cost effective process for biaryl-hydrazine unit {tert-butyl 2-[4-(2-pyridinyl)benzyl]hydrazinecarboxylate} of atazanavir on a large scale. The synthesis involved palladium catalyzed Suzuki-Miyaura coupling of 2-chloropyridine and (4-cyanophenyl)boronic acid followed by DIBAL-H reduction of cyano group to aldehyde which is then treated with tert-butyl carbazate to furnish hydrazone subsequently in situ reduction with NaBH4. A large scale synthesis of biaryl-hydrazine unit of atazanavir was accomplished in three steps with 71% overall yield. We have developed a short and efficient synthesis of atazanavir key intermediate biaryl-hydrazine unit. The process does not require the usage of Grignard reagent, expensive catalyst, protection/deprotection of aldehyde moiety and catalytic hydrogenation.

Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical

This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.

Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides

Organic halides are important building blocks in synthesis, but their use in (photo)redox chemistry is limited by their low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates in radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that a-aminoalkyl radicals, easily accessible from simple amines, promote the homolytic activation of carbon-halogen bonds with a reactivity profile mirroring that of classical tin radicals. This strategy conveniently engages alkyl and aryl halides in a wide range of redox transformations to construct sp3-sp3, sp3-sp2, and sp2-sp2 carbon-carbon bonds under mild conditions with high chemoselectivity.