1202-34-2

Basic information

• Product Name: 2,2'-DIPYRIDYLAMINE
• Synonyms: 2-(2-pyridylamino)pyridine;2,2’-bipyridylamine;2,2'-Bipyridylamine;2-Pyridinamine, N-2-pyridinyl-;bis(2-pyridyl)amine;bis(o-pyridyl)amine;Di(2-pyridyl)amine;di-2-pyridylamine
• CAS NO: 1202-34-2
• Molecular Formula: C₁₀H₉N₃
• Molecular Weight: 171.2
• EINECS: 214-864-3
• Product Categories: Heterocyclic Compounds;C9 to C46;Heterocyclic Building Blocks;Pyridines;Amines;Aromatics;Chelating Agents & Ligands;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1202-34-2.mol

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 222 °C50 mm Hg(lit.)
• Flash Point: 170 °C
• Appearance: /
• Density: 1.1984 (rough estimate)
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.79±0.10(Predicted)
• BRN: 127131
• CAS DataBase Reference: 2,2'-DIPYRIDYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIPYRIDYLAMINE(1202-34-2)
• EPA Substance Registry System: 2,2'-DIPYRIDYLAMINE(1202-34-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3545
• WGK Germany: 3
• RTECS: UR3545000
• Hazardous Substances Data: 1202-34-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
2,2'-Dipyridylamine is used as a metal-complexing agent, specifically as an effective iron chelating agent to help protect against UVB radiation. It is also an impurity of Chlorpheniramine Maleate (C424300).
Used in Pharmaceutical Industry:
2,2'-Dipyridylamine is used as a pharmaceutical secondary standard for application in quality control, providing pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Used in Catalyst Synthesis:
2,2'-Dipyridylamine (bipyam) can be used as a bidentate N-donor ligand in the synthesis of various metal complexes, such as Pd-polyoxovanadates. These complexes serve as heterogeneous catalysts for the oxidation of benzylic hydrocarbons.

Formation

2,2′-Dipyridylamine can be formed by heating?pyridine?with?sodium amide. Alternatively,?2-aminopyridine?can be heated with?2-chloropyridine?over?barium oxide.

Purification Methods

Crystallise the amine from *benzene or toluene [Blakley & De Armond J Am Chem Soc 109 4895 1987]. The amine is also recrystallised from Me2CO (m 95.1o) or distilled in a vacuum. [Beilstein 22 I 630, 22 II 331, 22 III/IV 3961.]

Upstream product

• 110-86-1 pyridine 
• 40825-17-0 Natrium-Verbindung des [2]Pyridylamins 
• 504-29-0 2-aminopyridine 
• 109-09-1 2-chloropyridine 
• 108-88-3 toluene 
• 526-99-8 meso-galactaric acid 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 60136-19-8 Co(di-(2-pyridyl)amine)2⁽²⁺⁾ 
• 1193779-41-7 diethyl [2-(pyridin-2-ylamino)-5-methylpyridin-3-yl]phosphonate 
• 14150-95-9 2-aminopyridine N-oxide 
• 1205-41-0 2-(pyridin-2-ylamino)pyridine 1-oxide 
• 694-59-7 pyridine N-oxide 
• 41122-56-9 sodium 2-pyridine diazotate 
• 58996-80-8 N-p-tolylsulfonyl-2,2'-dipyridylamine 

Downstream Products

• 557767-01-8 N,N'-bis(2,2'-dipyridyl)trimesoylamide 
• 432551-42-3 2,4,6-tris(2,2'-dipyridylamino)-benzene 
• 684243-06-9 3,5-bis(2,2'-dipyridylamino)bromobenzene 
• 936008-61-6 [Ag₂(bis(2-pyridyl)amine)2(dppp)(ClO₄)2] 
• 936007-86-2 [Ag(NO₃)(AsPh₃)(bis(2-pyridyl)amine)] 
• 936007-93-1 [Ag(NO₃)(P(cyclohexyl)3)(bis(2-pyridyl)amine)] 
• 936007-83-9 [Ag(NO₃)(PPh₃)(bis(2-pyridyl)amine)] 
• 936007-88-4 [Ag(NO₃)(SbPh₃)(bis(2-pyridyl)amine)] 
• 402507-19-1 [Cu(2,2'-dipyridylamine)(2-chloro-5-methylthiobenzoate)Br] 
• 863184-77-4 [Ni(2,2'-bipyridylamine)(p-hydroxybenzenecarboxylate)(H₂O)2](NO₃)*H₂O 
• 199916-69-3 [ReCl(CO)2(P(C₆H₅)3)(C₁₀H₉N₃)] 
• 1334333-91-3 [Cu(2-[(2,3-dimethylphenyl)amino]benzoate)2(2,2'-bipyridylamine)]*MeOH 
• 1616245-51-2 [Ni(μ-Cl){2,2′-dipyridyl-N-benzylamine}Cl]2 
• 1616245-52-3 [Ni(μ-Cl){2,2'-dipyridyl-N-methylcyclohexylamine}Cl]2 

Relevant articles and documents

Synthesis of Novel D-π-A chromophores: Effect of structural manipulations on photophysical properties, viscosity and DFT study

Four novel push-pull D-π-A type chromophores namely (E)-2-cyano-3-(4-(di(pyridin-2-yl)amino)phenyl)acrylic acid (BECA), (E)-2-(5-(4-(di(pyridin-2-yl)amino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (BERA), (E)-2-cyano-3-(5-(di(pyridin-2-yl)amino)thiophen-2-yl)acrylic acid (THCA) and (E)-2-(5-((5-(di(pyridin-2-yl)amino)thiophen-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (THRA) were synthesized. The dyes synthesize were characterized by HR-MS, 1H NMR, and 13C NMR spectroscopies. The synthesized dyes show absorption and emission wavelength in the range of 362–499 nm and 471–557 nm respectively. The chromophores BECA and BERA show a large stroke shift (63–130 nm) as compared to chromophores THCA and THRA (38–62 nm). Oscillator strengths (f), transition dipole moments (μeg), and different solvent polarity plots have been investigated for understanding intramolecular charge transfer (ICT) characteristics from donor to the acceptor. Interestingly, the viscosity induced emission for all four chromophores were observed in ethanol: polyethylene - 400 solvent mixtures. The computational study of these chromophores was carried out by using density functional theory (DFT) along with time-dependent density functional theory (TD-DFT).

Effect of structural manipulation in hetero-tri-aryl amine donor-based D-A′-π-A sensitizers in dye-sensitized solar cells

The role of hetero-atom manipulation/hetero-aryl group insertion in the triarylamine to obtain hetero triarylamine as a donor in highly efficient photosensitizers was investigated to study the structure-efficiency relationship in dye-sensitized solar cells (DSSCs). A newly synthesized sensitizer was explored containing N-phenyl-N-(pyridin-2-yl) pyridine-2-amine (DPPA) and N-(pyridin-2-yl)-N-(thiophen-2-yl) pyridine-2-amine (DPTA) as the donor along with a strong electron-withdrawing cyano group (-CN) as the auxiliary acceptor group and cyanoacetic acid and rhodamine-3-acetic acid as anchoring groups. The triphenylamine donor was manipulated for the first time with the insertion of a nitrogen atom in the aryl ring for DSSCs. These hetero-aryl-based sensitizers showed a significant improvement in the photophysical as well as photovoltaic performance. The replacement of cyanoacetic acid by rhodanine-3-acetic acid as an anchoring unit resulted in a significant red-shift in absorption as well as emission maxima. The methylene group in rhodanine-3-acetic acid interrupted the LUMO delocalization on the anchoring group in sensitizers DP3 and DP4, as shown by DFT calculations. The presence of cyanoacetic acid in sensitizers DP1 and DP2 showed effective charge transfer from HOMO to LUMO and efficient electron injection from LUMO to the conduction band of the TiO2 semiconductor. The sensitizer DP2 showed a maximum efficiency of 4.7%, a short-circuit current Jsc = 11.78 mA cm-2, an open-circuit voltage Voc = 0.608 V and a fill factor FF = 0.62. The enhanced efficiency of sensitizer DP2 was attributed to the presence of the strong electron-withdrawing cyanoacetic acid anchoring group and the presence of the thiophene linker at the N-aryl core.

Reductive acylamination of pyridine N-oxide with aminopyridines and their N-p-tolylsulfonyl derivatives

Pyridine N-oxide reacts with 2- and 3-aminopyridines and their N-p-tolylsulfonyl derivatives in alkaline medium in the presence of p-toluenesulfonyl chloride to give N-p-tolylsulfonyl-2,2′- and 2,3′-dipyridylamines, respectively, as a result of reductive acylamination. In the reactions with 4-aminopyridine and 4-p-tolylsulfonyl- aminopyridine, their N-p-tolylsulfonyl- and N,N-bis(p-tolylsulfonyl) derivatives are formed, while reductive acylamination does not occur. 2005 Pleiades Publishing, Inc.

Hybrid organic-inorganic Cu(II) iminoisonicotine@TiO2@Fe3O4 heterostructure as efficient catalyst for cross-couplings

Two novel mononuclear copper (II) complex catalysts were synthesized from a new tridentate iminoisonicotine ligand (HL) by coordination with Cu(II) ion, with (CuL@TiO2@Fe3O4) and without (CuL) immobilization on TiO2-coated nanoparticles of Fe3O4. The ester moiety on the back of the ligand was utilized for immobilization on nanoparticles of Fe3O4. Both ligand and CuL complex were fully characterized by using?alternative spectral techniques (nuclear magnetic resonance, infrared, ultraviolet-visible and mass spectroscopy, and elemental analyses). Different analytical techniques were used to identify the structural feature and morphology of the immobilized copper catalyst (CuL@TiO2@Fe3O4) shell-shell-core system. The structural analysis revealed that the catalyst system is composed of both agglomerated nanospheres and deformed nanorods. Both copper catalysts, immobilized CuL@TiO2@Fe3O4 and un-immobilized CuL were studied in heterogeneous and homogeneous catalysis, respectively, for Suzuki-Miyaura (C–C) and Buchwald-Hartwig (C–N) cross-coupling reactions of various heteroaryl halides. Both catalysts showed good catalytic potential under the controlled optimal reaction conditions. In contrast to the homogeneous catalyst (CuL), the heterogeneous catalyst (CuL@TiO2@Fe3O4) showed slightly better catalytic performance. The characteristic obtains supported the catalytic potential of the current samples. Reusability/recycling of both catalysts was also investigated in C–C cross-coupling reactions. It was found that the homogeneous catalyst (CuL) could be only recycled up to three times, whereas the heterogeneous one (CuL@TiO2@Fe3O4) could be reused up to seven times with good efficiency.

Sequential amination of heteroaromatic halides with aminopyridine 1-oxides and their N-protected derivatives based on novel aza-Smiles rearrangement

The SNAr and Pd-catalyzed amination of chloro derivatives of azines, diazines, and triazines with 2-aminopyridine 1-oxides and their N-protected derivatives was described.

Synthesis, characterization, and photoluminescent studies of three-coordinate Cu(i)-NHC complexes bearing unsymmetrically-substituted dipyridylamine ligands

A series of heteroleptic three-coordinate Cu(i) complexes bearing monodentate N-heterocyclic carbene (NHC) ligands of the type 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) and 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr), and bidentate N-donor ligands of the type unsymmetrically-substituted dimethyl dipyridylamine (Me2Hdpa) and bis(mesityl)biazanaphthenequinone (mesBIAN) have been synthesized. The complexes [Cu(IPr)(3,4′-Me2Hdpa)]PF6, 1; [Cu(IPr)(3,5′-Me2Hdpa)]PF6, 2; [Cu(IPr)(3,6′-Me2Hdpa)]PF6, 3; [Cu(IPr)(mesBIAN)]PF6, 6; [Cu(SIPr)(3,4′-Me2Hdpa)]PF6, 7; [Cu(SIPr)(3,5′-Me2Hdpa)]PF6, 8; and [Cu(SIPr)(3,3′-Me2Hdpa)]PF6, 11 have been characterized by 1H and 13C NMR spectroscopies, elemental analysis, cyclic voltammetry, and photophysical studies in solid and solution phase. Single crystal X-ray structures were obtained for all complexes except 11. The crystallographic data reveal a mononuclear structure for all complexes with the copper atom ligated by one C and two N atoms. The UV-Vis absorption spectra of all dipyridylamine complexes in CH2Cl2 show a strong ligand-centered absorption band around 250 nm and a strong metal-to-ligand charge transfer (MLCT) band around 300 nm. When irradiated with UV light, the complexes exhibit strong emission maxima at 453-482 nm with photoluminescence quantum yields (PLQY) ranging from 0.21 to 0.87 in solid state. While the PLQY values are comparable to those of the symmetrical [Cu(IPr)(Me2Hdpa)]PF6 complexes, a stabilizing CH-π interaction has been reduced in the current systems. In particular, complex 3 lacks any strong CH-π interaction, but emits more efficiently than 1 and 2 wherein the interactions exist. Structural data analysis was performed to clarify the role of ligands' plane angle and the NH/CH?F interactions to the observed light interaction of unsymmetrical [Cu(NHC)(Me2Hdpa)]PF6 complexes. DFT calculations were performed to assist in the assignment of the electronic structure and excited state behavior of the complexes.

Pd-catalyzed N-arylation of heteroarylamines

(matrix presented) The palladium-catalyzed N-(hetero)arylation of a number of heteroarylamines including 2-aminopyridines, 2-aminothiazoles, and their analogues has been realized using Xantphos as the ligand. Weak bases such as Cs2CO3, Na2CO3, and K3PO4 were used in most cases to allow for the introduction of functional groups. Choice of the base and solvent was critical for the success of these reactions.

Towards rainbow photo/electro-luminescence in copper(i) complexes with the versatile bridged bis-pyridyl ancillary ligand

The synthesis and characterization of a family of copper(i) complexes bearing a bridged bis-pyridyl ancillary ligand is reported, highlighting how the bridge nature impacts the photo- A nd electro-luminescent behaviours within the family. In particular, the phosphonium bridge led to copper(i) complexes featuring good electrochemical stability and high ionic conductivity, as well as a stark blue-to-orange luminescence shift compared to the others. This resulted in high performance light-emitting electrochemical cells reaching stabilities of 10 mJ at ca. 40 cd m-2 that are one order of magnitude higher than those of the other complexes. Overall, this work sheds light onto the crucial role of the bridge nature of the bis-pyridyl ancillary ligand on the photophysical features, film forming and, in turn, on the final device performances.

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