Home Pyridines 19437-26-4
19437-26-4,MFCD00006288
Catalog No.:AA003P80

19437-26-4 | Di-2-pyridyl ketone

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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Application
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003P80
Chemical Name:
Di-2-pyridyl ketone
CAS Number:
19437-26-4
Molecular Formula:
C11H8N2O
Molecular Weight:
184.1940
MDL Number:
MFCD00006288
SMILES:
O=C(c1ccccn1)c1ccccn1
NSC Number:
174057
Properties
Properties
 
BP:
343.5°C at 760 mmHg  
Form:
Liquid  
MP:
52-55 °C(lit.);  
Storage:
Room Temperature;  

Computed Properties
 
Complexity:
186  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
1.8  

Upstream Synthesis Route

[1]Patent:WO2016/190630,2016,A1,.Locationinpatent:Paragraph258;259;260

[2]Patent:WO2018/175311,2018,A1,.Locationinpatent:Paragraph0134

[3]DaltonTransactions,2016,vol.45,#34,p.13604-13614

[4]JournaloftheChemicalSociety,DaltonTransactions:InorganicChemistry(1972-1999),1991,#4,p.1165-1166

[5]DaltonTransactions,2012,vol.41,#3,p.1065-1073

[6]JournaloftheAmericanChemicalSociety,2016,vol.138,#28,p.8781-8788

[7]Patent:US2017/81326,2017,A1,.Locationinpatent:Paragraph0179;0182

[8]InorganicChemistry,2018,vol.57,#18,p.11761-11774

[1]JournalofOrganicChemistry,1983,vol.48,#17,p.2941-2942

[1]DaltonTransactions,2015,vol.44,#6,p.2724-2736

[1]JournalofOrganicChemistry,1987,vol.52,#13,p.2790-2796

[1]Chemistry-AEuropeanJournal,2018,vol.24,#37,p.9269-9273

Downstream Synthesis Route

[1]CanadianJournalofChemistry,1952,vol.30,p.563,570

[1]JournalofOrganicChemistry,1983,vol.48,p.2941-2942

19437-26-4    304-20-1   
2,2'-Dipyridyl-1-phthalazinohydrazonedihydrochloride 

[1]BulletindelaSocieteChimiquedeFrance,1990,p.38-42

19437-26-4    55-59-4   
1-(2'-Pyridyl)-3-(3',4'-dimethoxyphenyl)-2-azaindolizine 

[1]Tetrahedron,1992,vol.48,p.10423-10430

[1]JournalofHeterocyclicChemistry,1983,vol.20,p.1295-1302

Literature

Title: The 'periodic table' of di-2-pyridyl ketone: vanadium complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20121021

Title: Exploring synthetic pathways to cationic heteroleptic cyclometalated iridium complexes derived from dipyridylketone.

Journal: Dalton transactions (Cambridge, England : 2003) 20120621

Title: Direct functionalization of M-C (M = Pt(II), Pd(II)) bonds using environmentally benign oxidants, O2 and H2O2.

Journal: Accounts of chemical research 20120619

Title: A heterometallic (Ni(II)-Cu(II)) decanuclear cluster containing two distorted cubane-like pentanuclear cores: synthesis, structure, and magnetic properties.

Journal: Inorganic chemistry 20120618

Title: Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity.

Journal: Dalton transactions (Cambridge, England : 2003) 20120607

Title: Poly[[(μ(2)-di-3-pyridyl-methanone-κN:N')(μ(2)-hexa-fluoro-silicato-κF:F')copper(II)] dihydrate].

Journal: Acta crystallographica. Section E, Structure reports online 20120201

Title: Dipyridylketone as a versatile ligand precursor for new cationic heteroleptic cyclometalated iridium complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20120121

Title: trans-Tetra-aqua-bis-[bis-(pyridin-3-yl)methanone-κN]manganese(II) bis-(perchlorate).

Journal: Acta crystallographica. Section E, Structure reports online 20120101

Title: Synthesis, Characterization and In Vitro Antibacterial Studies of Organotin(IV) Complexes with 2-Hydroxyacetophenone-2-methylphenylthiosemicarbazone (H(2)dampt).

Journal: Bioinorganic chemistry and applications 20120101

Title: catena-Poly[[bis-(2,4-dichloro-benzoato)bis-(methanol-κO)cobalt(II)]-μ-4,4'-bipyridine-κN:N'].

Journal: Acta crystallographica. Section E, Structure reports online 20111201

Title: catena-Poly[(dichloridozinc)-μ-bis-(pyridin-3-yl)methanone-κN:N'].

Journal: Acta crystallographica. Section E, Structure reports online 20111201

Title: Bis(methanol-κO)bis-(quinoline-2-carboxyl-ato-κN,O)nickel(II).

Journal: Acta crystallographica. Section E, Structure reports online 20111101

Title: Novel thiosemicarbazone iron chelators induce up-regulation and phosphorylation of the metastasis suppressor N-myc down-stream regulated gene 1: a new strategy for the treatment of pancreatic cancer.

Journal: Molecular pharmacology 20111001

Title: Expanding the 3d-4f heterometallic chemistry of the (py)2CO and pyCOpyCOpy ligands: structural, magnetic and Mössbauer spectroscopic studies of two Fe(II)-Gd(III) complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20110828

Title: Tetrabutylammonium fluoride (TBAF)-catalyzed addition of substituted trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones.

Journal: The Journal of organic chemistry 20110603

Title: trans-Dichloridobis[(6-nicotinoyl-2-pyridyl-κN)(3-pyridyl-κN)methanone]copper(II).

Journal: Acta crystallographica. Section E, Structure reports online 20110601

Title: Hydrogencyanamido bridged multinuclear copper(II) complexes: from strong antiferromagnetic couplings to weak ferromagnetic couplings.

Journal: Dalton transactions (Cambridge, England : 2003) 20110521

Title: High-spin Ni(II) clusters: triangles and planar tetranuclear complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20110507

Title: Remote functionalisation via sodium alkylamidozincate intermediates: access to unusual fluorenone and pyridyl ketone reactivity patterns.

Journal: Chemical communications (Cambridge, England) 20110407

Title: catena-Poly[[tetra-aqua-[trans-1,2-bis-(4-pyrid-yl)ethene-κN:N']nickel(II)] dinitrate].

Journal: Acta crystallographica. Section E, Structure reports online 20110401

Title: Defective dicubane-like tetranuclear nickel(II) cyanate and azide nanoscale magnets.

Journal: Inorganic chemistry 20101220

Title: Nickel/lanthanide single-molecule magnets: {Ni(3)Ln} 'stars' with a ligand derived from the metal-promoted reduction of di-2-pyridyl ketone under solvothermal conditions.

Journal: Inorganic chemistry 20101101

Title: Di-μ-iodido-bis{[hydroxy(methoxy)bis(2-pyridyl)methane-κN,O,N']iodidocadmium(II)}.

Journal: Acta crystallographica. Section E, Structure reports online 20101101

Title: Initial employment of di-2-pyridyl ketone as a route to nickel(II)/lanthanide(III) clusters: triangular Ni(2)Ln complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20101007

Title: Bis(di-2-pyridyl-methane-diol-κN,O,N')nickel(II) dibenzoate.

Journal: Acta crystallographica. Section E, Structure reports online 20101001

Title: Dibenzoatobis[3-(pyrrol-1-ylmeth-yl)pyridine]-zinc(II).

Journal: Acta crystallographica. Section E, Structure reports online 20100801

Title: Comparison of clinically used and experimental iron chelators for protection against oxidative stress-induced cellular injury.

Journal: Chemical research in toxicology 20100621

Title: Synthesis, characterization, and photophysical properties of three platinum(II) complexes bearing fluorescent analogues of the Di-2-pyridylmethane ligand.

Journal: Inorganic chemistry 20100607

Title: Rare oxidation-state combinations and unusual structural motifs in hexanuclear Mn complexes using 2-pyridyloximate ligands.

Journal: Inorganic chemistry 20100517

Title: Polynuclear copper(II) complexes of di-2-pyridyl ketone derivatives and tert-butylphosphonic acid: crystal structures and magnetic behaviour.

Journal: Dalton transactions (Cambridge, England : 2003) 20100507

Title: 4-(3,3-Dimethyl-perhydro-1,3-oxa-zolo[3,4-a]pyridin-1-yl)-2,8-bis-(tri-fluoro-meth-yl)quinoline.

Journal: Acta crystallographica. Section E, Structure reports online 20100301

Title: Environmental transcriptome analysis reveals physiological differences between biofilm and planktonic modes of life of the iron oxidizing bacteria Leptospirillum spp. in their natural microbial community.

Journal: BMC genomics 20100101

Title: Synthesis and Characterization of a Linear [Mn(3)(O(2)CMe)(4)(py)(8)] Complex.

Journal: Bioinorganic chemistry and applications 20100101

Title: Mononuclear and Dinuclear Manganese(II) Complexes from the Use of Methyl(2-pyridyl)ketone Oxime.

Journal: Bioinorganic chemistry and applications 20100101

Title: Use of the 2-Pyridinealdoxime/N,N'-Donor Ligand Combination in Cobalt(III) Chemistry: Synthesis and Characterization of Two Cationic Mononuclear Cobalt(III) Complexes.

Journal: Bioinorganic chemistry and applications 20100101

Title: Tetra-μ-benzoato-bis-{[4-(pyrrolidin-1-yl)pyridine]zinc(II)}.

Journal: Acta crystallographica. Section E, Structure reports online 20100101

Title: N-hetero atomic effect on the photophysics of 2,2'-dipyridylketone.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20091201

Title: Tetra-μ-benzoato-bis-{[trans-1-(2-pyrid-yl)-2-(4-pyrid-yl)ethyl-ene]zinc(II)}.

Journal: Acta crystallographica. Section E, Structure reports online 20091201

Title: Bis[μ-1,2-diphenyl-N,N'-bis-(di-2-pyridyl-methyl-eneamino)ethane-1,2-diimine]disilver(I) bis-(hexa-fluorido-phosphate) acetonitrile disolvate.

Journal: Acta crystallographica. Section E, Structure reports online 20091201

Title: N'-(Di-2-pyridylmethyl-ene)benzo-hydrazide.

Journal: Acta crystallographica. Section E, Structure reports online 20090701

Title: Tris(phenyl 2-pyridyl ketone oxime-κN,N')cadmium(II) dinitrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: Bis(di-2-pyridylmethane-diol-κN,O,N')copper(II) bis-(tetra-fluorido-borate) dihydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: A neutral cubane with a Zn(4)O(4) core: tetra-benzoato-tetra-kis(μ(3)-hydroxydi-2-pyridylmethano-lato)tetra-zinc(II)-acetone-methanol (1/2/1).

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: Bis(di-2-pyridylmethane-diol-κN,O,N')nickel(II) dinitrate.

Journal: Acta crystallographica. Section E, Structure reports online 20090601

Title: Azide groups in higher oxidation state manganese cluster chemistry: from structural aesthetics to single-molecule magnets.

Journal: Inorganic chemistry 20090420

Title: Molecular sensing behavior of di-2-pyridyl ketone p-aminophenylhydrazone hydrate (dpkabh.H2O) in non-aqueous media.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20090201

Title: A MnII4 cubane and a novel MnII10MnIII4 cluster from the use of di-2-pyridyl ketone in manganese acetate chemistry.

Journal: Dalton transactions (Cambridge, England : 2003) 20090114

Title: Diffusion and NOE NMR studies on multicationic DAB-organoruthenium dendrimers: size-dependent noncovalent self-assembly to megamers and ion pairing.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: Unusual structural types in nickel cluster chemistry from the use of pyridyl oximes: Ni5, Ni12Na2, and Ni14 clusters.

Journal: Inorganic chemistry 20081215

Title: Bis(di-2-pyridylmethane-diol-κN,O,N')copper(II) dl-tartrate.

Journal: Acta crystallographica. Section E, Structure reports online 20081201

Title: Diol-type ligands as central 'players' in the chemistry of high-spin molecules and single-molecule magnets.

Journal: Dalton transactions (Cambridge, England : 2003) 20081107

Title: High nuclearity single-molecule magnets: a mixed-valence Mn26 cluster containing the di-2-pyridylketone diolate dianion.

Journal: Inorganic chemistry 20081103

Title: [Bi5(dpd)6 within CH3CN](ClO4)3.3CH3CN: a supramolecular, tetrahedral pentabismuth cluster derived from a nonabismuth oxo/hydroxide.

Journal: Dalton transactions (Cambridge, England : 2003) 20081014

Title: Di-2-pyridyl ketone/benzoate/azide combination as a source of copper(II) clusters and coordination polymers: dependence of the product identity on the solvent.

Journal: Inorganic chemistry 20080915

Title: Novel mixed-valence manganese cluster with two distinct Mn3(II/III/II) and Mn3(III/II/III) trinuclear units in a pseudocubane-like arrangement.

Journal: Inorganic chemistry 20080901

Title: catena-Poly[[μ-bromido-(μ-hydroxydi-2-pyridylmethano-lato-κN,O:O,N')dicopper(II)(Cu-Cu)]-di-μ-bromido].

Journal: Acta crystallographica. Section E, Structure reports online 20080901

Title: Di-μ-bromido-bis-[bromido(di-2-pyridylmethane-diol-κN,N')copper(II)] dihydrate.

Journal: Acta crystallographica. Section E, Structure reports online 20080901

Title: Vibrational dynamics and structural investigation of 2,2'-dipyridylketone using Raman, IR and UV-visible spectroscopy aided by ab initio and density functional theory calculation.

Journal: The Journal of chemical physics 20080414

Title: Synthesis, structure and interactions with DNA of novel tetranuclear, [Mn4(II/II/II/IV)] mixed valence complexes.

Journal: Journal of inorganic biochemistry 20080401

Title: Photophysical and electrochemical properties of new ortho-metalated complexes of rhodium(III) containing 2,2'-dipyridylketone and 2,2'-dipyridylamine. An experimental and theoretical study.

Journal: Dalton transactions (Cambridge, England : 2003) 20070821

Title: Di-2-pyridyl ketone oxime in copper chemistry: di-, tri-, penta- and hexanuclear complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20070707

Title: Acetate/di-2-pyridyl ketone oximate 'blend' as a source of high-nuclearity nickel(II) clusters: dependence of the nuclearity on the nature of the inorganic anion present.

Journal: Inorganic chemistry 20070402

Title: A mononuclear and a mixed-valence chain polymer arising from copper(II) halide chemistry and the use of 2,2'-pyridil.

Journal: Bioinorganic chemistry and applications 20070101

Title: In situ synthesis of trisubstituted methanol ligands and their potential as one-pot generators of cubane-like metal complexes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060918

Title: 2,2'-Dipyridylketone (dpk) as ancillary acceptor and reporter ligand in complexes [(dpk)(Cl)Ru(mu-tppz)Ru(Cl)(dpk)]n+ where tppz = 2,3,5,6-tetrakis(2-pyridyl)pyrazine.

Journal: Inorganic chemistry 20060918

Title: Reactivity and structural and physical studies of tetranuclear iron(III) clusters containing the [Fe4(mu3-O)2]8+ 'butterfly' core: an FeIII4 cluster with an S = 1 ground state.

Journal: Inorganic chemistry 20060904

Title: Two chiral metal clusters derived from nucleophilic addition of L-proline to di-2-pyridyl ketone.

Journal: Inorganic chemistry 20060821

Title: Manganese(II) complexes of substituted di-2-pyridyl ketone thiosemicarbazones: structural and spectral studies.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060501

Title: Structural and spectral perspectives of a novel thiosemicarbazone synthesized from di-2-pyridyl ketone and 4-phenyl-3-thiosemicarbazide.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20060101

Title: Polymorphic di-2-pyridyl ketone 4-nitrophenylhydrazone (dpknph): the structure of beta-dpknph.

Journal: Acta crystallographica. Section C, Crystal structure communications 20051001

Title: Complex series [Ru(tpy)(dpk)(X)]n+ (tpy = 2,2':6',2''-terpyridine; dpk = 2,2'-dipyridyl ketone; X = Cl-, CH3CN, NO2(-), NO+, NO*, NO-): substitution and electron transfer, structure, and spectroscopy.

Journal: Inorganic chemistry 20050822

Title: The first cobalt metallacrowns: preparation and characterization of mixed-valence cobalt(II/III), inverse 12-metallacrown-4 complexes.

Journal: Inorganic chemistry 20050516

Title: Dinuclear versus tetranuclear cluster formation in zinc(II) nitrate/di-2-pyridyl ketone chemistry: synthetic, structural and spectroscopic studies.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050501

Title: Synthesis and structure-activity correlation studies of metal complexes of alpha-N-heterocyclic carboxaldehyde thiosemicarbazones in Shewanella oneidensis.

Journal: International journal of environmental research and public health 20050501

Title: Highly efficient and direct heterocyclization of dipyridyl ketone to N,N-bidentate ligands.

Journal: The Journal of organic chemistry 20050318

Title: Mono- and dinuclear tricarbonyltechnetium(I) complexes with thiosemicarbazones.

Journal: Inorganic chemistry 20050221

Title: Di-2-pyridyl ketone oxime [(py)2CNOH] in manganese carboxylate chemistry: mononuclear, dinuclear and tetranuclear complexes, and partial transformation of (py)2CNOH to the gem-diolate(2-) derivative of di-2-pyridyl ketone leading to the formation of NO3-.

Journal: Dalton transactions (Cambridge, England : 2003) 20050207

Title: A novel high-spin heterometallic Ni12K4 cluster incorporating large Ni-azide circles and an in situ cyanomethylated di-2-pyridyl ketone.

Journal: Chemical communications (Cambridge, England) 20050114

Title: Di-2-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone.

Journal: Acta crystallographica. Section C, Crystal structure communications 20041201

Title: Synthesis of heteroleptic bis(diimine)carbonylchlororuthenium(II) complexes from photodecarbonylated precursors.

Journal: Inorganic chemistry 20040503

Title: Synthesis of Pt(dpk)Cl(4) and the reversible hydration to Pt(dpk-O-OH)Cl(3).H-phenCl: X-ray, spectroscopic, and electrochemical characterization.

Journal: Inorganic chemistry 20040112

Title: A cationic 24-MC-8 manganese cluster with ring metals possessing three oxidation states [Mn(II)4Mn(III)6Mn(IV)2(mu4-O)2(mu3-O)4(mu3-OH)4(mu3-OCH3)2(pko)12](OH)(ClO4)3.

Journal: Chemical communications (Cambridge, England) 20031107

Title: Dipyridylketone binding and subsequent C-C bond insertion reactions at cyclopentadienylrhodium.

Journal: Chemical communications (Cambridge, England) 20030921

Title: Octanuclearity and tetradecanuclearity in manganese chemistry: an octanuclear manganese(II)/(III) complex featuring the novel [Mn8(mu4-O)2(mu3-OH)2]14+ core and [Mn10(II)Mn4(III)O4(O2CMe)20[(2-py)2C(OH)O]4] (2-py = 2-pyridyl).

Journal: Chemical communications (Cambridge, England) 20030407

Title: Identification of the di-pyridyl ketone isonicotinoyl hydrazone (PKIH) analogues as potent iron chelators and anti-tumour agents.

Journal: British journal of pharmacology 20030301

Title: Reactivity in polynuclear transition metal chemistry as a means to obtain high-spin molecules: substitution of mu 4-OH- by eta 1,mu 4-N3- increases nine times the ground-state S value of a nonanuclear nickel(II) cage.

Journal: Chemical communications (Cambridge, England) 20011207

Title: Dicubane-like tetrameric cobalt(II)-pseudohalide ferromagnetic clusters.

Journal: Inorganic chemistry 20010827

Application
Di(2-pyridyl) ketone serves as a versatile ligand in coordination chemistry, facilitating the synthesis of various metal complexes with unique structures and properties. It has been utilized in the preparation of unusual {Ni(II)(3)Ln(III)(μ-OR)(6)}(3+) complexes featuring a "star" topology, demonstrating its ability to coordinate with both nickel and lanthanide ions to form intricate molecular architectures. Additionally, its monoanionic form has been employed in the synthesis of triangular Ni(2)M (M = lanthanide, Y) complexes, highlighting its utility in the construction of multinuclear metal complexes.

In terms of biochemistry and physiology, Schiff base ligands derived from di(2-pyridyl) ketone exhibit notable antiproliferative activity in SK-N-MC neuroepithelioma (cancer) cells. This biological activity underscores the potential pharmacological relevance of compounds containing the di(2-pyridyl) ketone moiety in cancer therapy and drug development efforts. Overall, di(2-pyridyl) ketone emerges as a valuable ligand in coordination chemistry, offering a platform for the design and synthesis of metal complexes with diverse structural motifs and biological activities.
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Tags:19437-26-4 Molecular Formula|19437-26-4 MDL|19437-26-4 SMILES|19437-26-4 Di-2-pyridyl ketone |Organic_Building_Blocks