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
• Article Data: 49

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

Description

2,2'-Dipyridylamine, also known as bipyam, is an organic compound with the formula (C5H4N)2NH. It consists of a pair of 2-pyridyl groups (C5H4N) linked to a secondary amine. The compound forms a range of coordination complexes, and its conjugate base, 2,2'-dipyridylamide, forms extended metal atom chains. It is a white solid and is used as a pharmaceutical secondary standard for quality control in pharmaceutical laboratories and manufacturers.

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

• 504-29-0 2-aminopyridine 
• 109-09-1 2-chloropyridine 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 109-04-6 2-bromo-pyridine 
• 75-44-5 phosgene 
• 98-82-8 Isopropylbenzene 
• 40825-17-0 Natrium-Verbindung des [2]Pyridylamins 
• 526-99-8 meso-galactaric acid 
• 41122-56-9 sodium 2-pyridine diazotate 
• 694-85-9 1-methyl-2-pyridone 
• 120777-38-0 Tl(2,2'-dipyridylamido) 
• 1679-09-0 1,1-dimethylpropanethiol 
• 108-98-5 thiophenol 
• 267664-37-9 [Ru(hedta)(dpa)]^(1-) 

Downstream Products

• 10428-50-9 tri-(2-pyridyl)amine 
• 73664-46-7 dipyrid-2-ylacetamide 
• 693289-13-3 N,N-dimethyl-N',N'-di-pyridin-2-yl-benzene-1,4-diamine 
• 916162-36-2 1,4-bis(di-2-pyridylaminomethyl)benzene 
• 609769-95-1 N,N,N',N',N'',N''-hexa(2-pyridyl)-1,3,5-tris(aminomethyl)benzene 
• 26422-90-2 N-benzyl-N-(pyridin-2-yl)pyridine-2-amine 
• 916162-33-9 1,2-bis(di-2-pyridylaminomethyl)benzene 
• 916162-34-0 1,3-bis(di-2-pyridylaminomethyl)benzene 
• 14363-27-0 [bis(N-phenyl-salicydenaminato)copper(II)] 
• 60101-12-4 2,2'-bipyridylcopper(II) phthalate 
• 200702-46-1 Au(C₁₀H₉N₃)(P(C₆H₅)3)⁽¹⁺⁾*ClO₄^(1-) = [Au(C₁₀H₉N₃)(P(C₆H₅)3)]ClO₄ 
• 616862-43-2 [Au2(C6F5)2(μ-2,2'-dipyridylamine)] 
• 849482-09-3 catena-poly[[(di-2-pyridylamine-κ2N,N')silver(I)]-mu.-2,6-dihydroxybenzoato-κ2O1:O2] 

Relevant articles and documents

The synthesis of aminopyridines: A method employing palladium-catalyzed carbon-nitrogen bond formation

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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.

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.

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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.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

In the present invention, provided is a novel compound capable of improving luminance efficiency, stability, and service life of an element, an organic electronic element using the same, and an electronic device thereof. By using the compound of the present invention, high luminance efficiency, low driving voltages, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved.

Phosphine Evaluation on a New Series of Heteroleptic Copper(I) Photocatalysts with dpa Ligand [Cu(dpa)(P,P)]BF4

Five new heteroleptic copper(I) complexes (C1-5) of the type [Cu(dpa)(P,P)]BF4 based on dipyridylamine (dpa) as N,N ligand and commercial diphosphines as P,P ancillary ligands have been synthesised through a simple methodology with high yields. All complexes were thoroughly characterised by spectroscopic and spectrometric techniques, as well by theoretical calculations. These showed Metal to Ligand Charge Transfer (MLCT) absorptions in the 300–370 nm region, and emission in the 450–520 nm region with quantum yields and lifetimes that depend on the nature of the P,P ligand. The photocatalytic performance of copper(I) complexes C1-5 was evaluated for their use as photoredox catalysts in ATRA reactions, decarboxylative coupling and an Appel-type reaction. The use of readily available dpa as N,N ligand constitutes an attractive alternative to the well-established phenanthroline ligands typically used in photocatalysis.