4411-83-0

Basic information

• Product Name: 6,6'-DICYANO-2,2'-BIPYRIDINE
• Synonyms: 6,6'-DICYANO-2,2'-BIPYRIDINE;2,2'-bipyridine-6,6'-dicarbonitrile;6,6'-dicyano-2,2'-bipyridine 97%;6,6'-Dicyano-2,2'-bipyridyl
• CAS NO: 4411-83-0
• Molecular Formula: C₁₂H₆N₄
• Molecular Weight: 206.21
• Mol File: 4411-83-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 257.0 to 261.0 °C
• Boiling Point: 436.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -1.80±0.22(Predicted)
• CAS DataBase Reference: 6,6'-DICYANO-2,2'-BIPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6'-DICYANO-2,2'-BIPYRIDINE(4411-83-0)
• EPA Substance Registry System: 6,6'-DICYANO-2,2'-BIPYRIDINE(4411-83-0)

Safety Data

• Hazardous Substances Data: 4411-83-0(Hazardous Substances Data)

Usage

General Description

6,6'-DICYANO-2,2'-BIPYRIDINE is a chemical compound with the molecular formula C12H6N2. It is a derivative of bipyridine and features two cyano groups at the 6 and 6' positions of the bipyridine ring. 6,6'-DICYANO-2,2'-BIPYRIDINE is widely used as a ligand in coordination chemistry and in the synthesis of metal-organic frameworks. It has a high affinity for transition metals and can be used to form stable complexes with a variety of metal ions. Additionally, 6,6'-DICYANO-2,2'-BIPYRIDINE has potential applications in organic electronic devices and as a building block in the construction of functional materials. However, it should be handled with care as it is toxic and potentially harmful if ingested or inhaled.

Upstream product

• 49669-22-9 6,6'-Dibromo-2,2'-bipyridine 
• 366-18-7 [2,2]bipyridinyl 
• 151-50-8 potassium cyanide 
• 7275-43-6 [2,2']bipyridinyl 1,1'-dioxide 
• 122918-25-6 6-bromopyridin-2-carbonitrile 
• 109-04-6 2-bromo-pyridine 
• 143-33-9 sodium cyanide 
• 77-78-1 dimethyl sulfate 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 1531633-61-0 [2,2'-bipyridine]-6,6'-diylbis(phenylmethanol) 
• 142593-07-5 dimethyl 2,2'-bipyridine-6,6'-dicarboxylate 
• 96517-97-4 6,6'-bis-(bromomethyl)-2,2'-bipyridine 
• 74065-64-8 6,6'-di(chloromethyl)-2,2'-bipyridine 
• 74065-63-7 6,6′-bis(hydroxymethyl)-2,2′-bipyridine 
• 65739-40-4 6,6′-bis(ethoxycarbonyl)-2,2′-bipyridine 
• 4479-74-7 2,2'-bipyridine-6,6'-dicarboxylic acid 

Relevant articles and documents

Structural studies of complex compounds of 6,6'-diacetyl-2,2'-bipyridine dioxime with copper(I/II), platinum(II), and palladium(II) metal ions

The tetradentate ligand 6,6'-diacetyl-2,2'-bipyridine dioxime (L) was obtained in high yield by the condensation reaction of 6,6'-diacetyl-2,2'- bipyridine with hydroxyl amine in alkaline solution. Density functional calculations and 3D modeling of the structure at the B3LYP/6-31G(d) level of theory for L revealed that the energy difference between the global trans conformer (trans-L), which possesses the C2h point group, and the distorted cis conformer (cis-L) was 5.214 kcal/mol. Synthesis and characterization of the metal complexes with Cu(I), Cu(II), Pt(II), and Pd(II) metal ions were reported. L acted as a N4- donor ligand to coordinate to the metal centers via N atoms of the 2,2'-bipyridine and the imine moieties to afford tetrahedral complex [CuI L]PF6 (1), distorted octahedral complex [CuII L(OH2)2](NO 3)2 (2), and square-planar complexes [PtII L]Cl2 (3) and [PdII L]Cl (4), respectively. The CHN analysis for 1 implies that L coordinated to 2 copper(I) ions as a bridging ligand to form a dinuclear metal complex, [Cu2L2] 2+, due to the twisting of the coordinated bonds exposed by the tetrahedral geometry preference for the metal ion. The ligand formed intramolecular hydrogen bonds between the oxime groups in 4, as revealed by the spectroscopic studies. The most stable conformations of the compounds were obtained by using the molecular mechanics optimization feature in CAChe software with an augmented MM2 force field. 1.

52. Influence of Chelating Groups on the Luminescence Properties of Europium(III) and Terbium(III) Chelates in the 2,2'-Bipyridine Series

Eight different 2,2'-bipyridine derivatives, i.e. 2, 5, 8, 10, 12, 13, 15, and 19 (Schemes 1 and 2), were prepared to study the influence of the chelating groups on the luminescence properties of their EuIII and TbIII chelates.According to our luminescence results, 2,2'-(methylenenitrilo)bis(acetic acid) as well as (methylenenitrilo)bis(methylphosphonic acid) in 6- and 6'-position of 2,2'-bipyridine is a suitable group when developing luminescent markers for bioaffinity assays based on time-resolved luminescence measurement.

Models of molecular photocatalysts for water oxidation: Strategies for conjugating the Ru(bda) fragment (bda = 2,2′-bipyridine-6,6′-dicarboxylate) to porphyrin photosensitizers

Model dyads, in which the Ru(bda) water oxidation catalyst (WOC) is connected to a porphyrin, were prepared following two different modular strategies: i) the direct linkage approach, in which porphyrins bearing peripheral pyridyl rings are bound to the {

Bis-(1,2,4-triazin-3-yl) ligand structure driven selectivity reversal between Am3+and Cm3+: solvent extraction and DFT studies

Selectivity between Am3+and Cm3+was investigated after their aqueous complexation with three structurally tailored hydrophilic bis-(1,2,4-triazin-3-yl) ligands followed by their extraction withN,N,N′N′-tetraoctyl diglycolamide (TODGA) dissolved in an ionic liquid (C4mim·Tf2N). The three hydrophilic ligands used were SO3PhBTP, SO3PhBTBP, and SO3PhBTPhen. It was evident from the solvent extraction studies that SO3PhBTP formed a stronger complex with Cm3+than with Am3+, but SO3PhBTPhen showed better complexation ability for Am3+than for Cm3+, and SO3PhBTBP showed no selectivity for the two actinide ions. DFT calculations indicated that the coordinating ‘N’atoms in BTP were more co-planar in the complex and this co-planarity was higher in the Cm3+complex as compared to that in Am3+. In the case of BTBP and BTPhen ligands, on the other hand, the co-planarity was more pronounced in the Am3+complexes. Mayer's bond order calculations of M-N bonds in the complexes also indicated a reversal of the complexation ability of the BTP and BTPhen ligands for Am3+and Cm3+. Calculations of the complexation energies further supported the higher selectivity of the BTP ligand for Am3+by ?52.0 kJ mol?1, and better selectivity of the BTPhen ligand for Cm3+by ?24.7 kJ mol?1

Uranyl Complexes with Aroylbis(N, N-dialkylthioureas)

The reaction of isophthaloylbis(N,N-diethylthiourea), H2L1, with UO2(CH3COO)2·2H2O and NEt3 as a supporting base gives a tetranuclear, anionic complex of the composition [{UO2(L1)}4(OAc)2]2-, in which the uranyl ions are S,O-chelate bonded. Each two of them are additionally linked by an acetato ligand. Similar reactions of various uranyl starting materials (uranyl acetate, uranyl nitrate, (NBu4)2[UO2Cl4]) with corresponding pyridine-centered ligands (pyridine-2,6-dicarbonylbis(N,N-dialkylthioureas), H2L2) yield mononuclear, neutral compounds, in which the thiourea derivatives are coordinated as S,N,N,N,S-five-dentate chelators. The equatorial coordination spheres of the formed hexagonal bipyramidal complexes [UO2(L2)(solv)] are completed by solvent ligands (H2O, MeOH, or DMF). Attempted reactions without a supporting base result in decomposition of the organic ligands and the formation of hexanuclear uranyl complexes with pyridine-2,6-dicarboxylato ligands, while the use of an excess of base results in condensation and the formation of dinuclear [{UO2(L2)(μ-OMe)}2]2- complexes. A stable complex of the composition [UO2(L3)] results from reactions of common uranyl starting materials with 2,2′-bipyridine-6,6′-dicarbonylbis(N,N-diethylthiourea) (H2L3). The equatorial coordination sphere of the neutral, hexagonal bipyramidal complex is occupied by an SN4S donor atom set, which is provided by the hexadentate organic ligand. While the uranium complexes with {L1}2- and {L2}2- are labile and rapidly decompose in acidic solutions, [UO2(L3)] is stable over a wide pH range, and the ligand readily extracts uranyl ions from aqueous solutions into organic solvents.