294648-03-6

Basic information

• Product Name: 4-(3-PYRIDYL)BENZONITRILE
• Synonyms: 4-(3-PYRIDINYL)BENZONITRILE;4-(3-PYRIDYL)BENZONITRILE;4-PYRIDIN-3-YL-BENZONITRILE;AKOS BAR-0419;4-(pyridin-3-yl)benzonitrile（WS203644）
• CAS NO: 294648-03-6
• Molecular Formula: C12H8N2
• Molecular Weight: 180.21
• Mol File: 294648-03-6.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 356.8°C at 760 mmHg
• Flash Point: 123.5°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 2.85E-05mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 4-(3-PYRIDYL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-PYRIDYL)BENZONITRILE(294648-03-6)
• EPA Substance Registry System: 4-(3-PYRIDYL)BENZONITRILE(294648-03-6)

Safety Data

• Hazardous Substances Data: 294648-03-6(Hazardous Substances Data)

Usage

General Description

4-(3-Pyridyl)benzonitrile is a chemical compound with the molecular formula C12H8N2. It is a nitrile derivative of pyridine and benzene, and is commonly used as a building block in organic synthesis. It plays a crucial role in the production of various pharmaceuticals, agrochemicals, and other fine chemicals. The compound possesses a nitrile functional group, which makes it a valuable intermediate for the synthesis of diverse organic compounds. 4-(3-Pyridyl)benzonitrile is also known for its ability to undergo various chemical reactions, making it a versatile and important compound in the field of organic chemistry.

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

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 329214-79-1 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1120-90-7 3-iodopyridine 
• 626-55-1 3-Bromopyridine 
• 126747-14-6 4-cyanophenylboronic acid 
• 67284-17-7 3-(tosyloxy)pyridine 
• 3058-39-7 4-iodobenzonitrile 
• 220565-63-9 pyridin-3-ylzinc(II) bromide 
• 110-86-1 pyridine 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 626-60-8 3-Chloropyridine 
• 623-03-0 4-Cyanochlorobenzene 
• 16518-17-5 potassium nicotinate 
• 5958-02-1 3-(4-methoxyphenyl)pyridine 

Relevant articles and documents

Arene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution

Herein we describe a cation radical-accelerated-nucleophilic aromatic substitution (CRA-SNAr) of alkoxy arenes utilizing a highly oxidizing acridinium photoredox catalyst and acetone cyanohydrin, an inexpensive and commercially available cyanide source. This cyanation is selective for carbon-oxygen (C-O) bond functionalization and is applicable to a range of methoxyarenes and dimethoxyarenes. Furthermore, computational studies provide a model for predicting regioselectivity and chemoselectivity in competitive C-H and C-O cyanation of methoxyarene cation radicals.

[2,2′-bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine

The ligand [2,2′-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.

Identification of Adenine and Benzimidazole Nucleosides as Potent Human Concentrative Nucleoside Transporter 2 Inhibitors: Potential Treatment for Hyperuricemia and Gout

To test the hypothesis that inhibitors of human concentrative nucleoside transporter 2 (hCNT2) suppress increases in serum urate levels derived from dietary purines, we previously identified adenosine derivative 1 as a potent hCNT2 inhibitor (IC50 = 0.64 μM), but further study was hampered due to its poor solubility. Here we describe the results of subsequent research to identify more soluble and more potent hCNT2 inhibitors, leading to the discovery of the benzimidazole nucleoside 22, which is the most potent hCNT2 inhibitor (IC50 = 0.062 μM) reported to date. Compound 22 significantly suppressed the increase in plasma uric acid levels after oral administration of purine nucleosides in rats. Because compound 22 was poorly absorbed orally in rats (F = 0.51%), its pharmacologic action was mostly limited to the gastrointestinal tract. These findings suggest that inhibition of hCNT2 in the gastrointestinal tract can be a promising approach for the treatment of hyperuricemia.