1802-29-5

Basic information

• Product Name: 2,2’-Bipyridine-5,5’-dicarbonitrile
• Synonyms: 2,2’-Bipyridine-5,5’-dicarbonitrile;6-(5-cyanopyridin-2-yl)pyridine-3-carbonitrile
• CAS NO: 1802-29-5
• Molecular Formula: C₁₂H₆N₄
• Molecular Weight: 206.20284
• EINECS: 200-258-5
• Mol File: 1802-29-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 272-273 °C
• Boiling Point: 414.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 0.12±0.32(Predicted)
• CAS DataBase Reference: 2,2’-Bipyridine-5,5’-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2’-Bipyridine-5,5’-dicarbonitrile(1802-29-5)
• EPA Substance Registry System: 2,2’-Bipyridine-5,5’-dicarbonitrile(1802-29-5)

Safety Data

• Hazardous Substances Data: 1802-29-5(Hazardous Substances Data)

Usage

General Description

2,2’-Bipyridine-5,5’-dicarbonitrile is a chemical compound that consists of two pyridine rings linked by a carbon-carbon double bond and each containing two cyano groups. It has a molecular formula of C14H8N4 and a molecular weight of 232.24 g/mol. 2,2’-Bipyridine-5,5’-dicarbonitrile is commonly used in coordination chemistry as a ligand to form metal complexes due to its ability to chelate with metal ions. It has been also used in organic synthesis and has potential applications in materials science and medicinal chemistry. 2,2’-Bipyridine-5,5’-dicarbonitrile is a yellow solid that is sparingly soluble in water but soluble in organic solvents such as acetone, ethanol, and dimethylformamide.

Upstream product

• 139585-70-9 2-bromo-5-cyanopyridine 
• 108-99-6 3-Methylpyridine 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 
• 1762-46-5 [2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester 
• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 15862-18-7 5,5'-dibromo-2,2'-dipyridyl 
• 143-33-9 sodium cyanide 
• 4444-36-4 2,2'-bipyridine-5,5'-bis(carboxamide) 
• 82799-91-5 5,5'-(2,2'-bipyridine)diacid chloride 

Relevant articles and documents

N-Rich Porous Polymer with Isolated Tb3+-Ions Displays Unique Temperature Dependent Behavior through the Absence of Thermal Quenching

The challenge of measuring fast moving or small scale samples is based on the absence of contact between sample and sensor. Grafting lanthanides onto hybrid materials arises as one of the most promising accurate techniques to obtain noninvasive thermometers. In this work, a novel bipyridine based porous organic polymer (bpyDAT POP) was investigated as temperature sensor after grafting with Eu(acac)3 and Tb(acac)3 complexes. The bpyDAT POP successfully showed temperature-dependent behavior in the 10–310 K range, proving the potential of amorphous, porous organic frameworks. We observed unique temperature dependent behavior. More intriguingly, instead of the standard observed change in emission as a result of a change in temperature for both Eu3+ and Tb3+, the emission spectrum of Tb3+ remained constant. This work provides framework- and energy-based explanations for the observed phenomenon. The conjugation in the bpyDAT POP framework is interrupted, creating energetically isolated Tb3+ environments. Energy transfer from Tb3+ to Eu3+ is therefore absent, nor energy back transfer from Tb3+ to bpyDAT POP ligand (i.e. no thermal quenching) is detected.

Syntheses of 5,5-disubstituted 2,2'-bipyridines

New and improved syntheses of 5,5'-donor-functionalized 2,2'-bipyridines are reported with the 5,5'-donors being -NH2 (4), -NMe2 (5), -CN (6), and - NCS (7). A new route for 4 and 5 is based on the coupling of 2-chloro-5- amino-pyridine in the presence of NiCl2 · 6 H2O/PPh3/Zn in DMF (NiCRA) · 6 was obtained by a dehydration treatment of 5,5'-dicarboxamide-2,2'- bipyridine with (F3CCO)2O and P4O10. The new ligand 7 is prepared from 4 and SCCl2.

Immobilization of Ir(I) complex on covalent triazine frameworks for C–H borylation reactions: A combined experimental and computational study

Metal-modified covalent triazine frameworks (CTFs) have attracted considerable attention in heterogeneous catalysis due to their strong nitrogen-metal interactions exhibiting superior activity, stability and hence recyclability. Herein, we report on a post-metalation of a bipyridine-based CTFs with an Ir(I) complex for C–H borylation of aromatic compounds. Physical characterization of the Ir(I)-based bipyCTF catalyst in combination with density functional theory (DFT) calculations exhibit a high stabilization energy of the Ir-bipy moiety in the frameworks in the presence of B2Pin2. By using B2Pin2 as a boron source, Ir(I)@bipyCTF efficiently catalyzed the C–H borylation of various aromatic compounds with excellent activity and good recyclability. In addition, XAS analysis of the Ir(I)@bipyCTF gave clear evidence for the coordination environment of the Ir.

Reductive couplings of 2-halopyridines without external ligand: Phosphine-free nickel-catalyzed synthesis of symmetrical and unsymmetrical 2,2'-bipyridines

An unexpectedly facile synthetic approach for symmetrical and unsymmetrical 2,2'-bipyridines through the Ni-catalyzed reductive couplings of 2-halopyridines was developed. The couplings were efficiently catalyzed by 5 mol % of NiCl2.6H2O without the use of external ligands. A variety of 2,2'-bipyridines including caerulomycin F have been efficiently synthesized.