1826-28-4

Usage

Uses

Used in Chemical Synthesis:
Phenyl 2-pyridyl ketoxime is used as a precursor in the preparation of inverse-9-metallacrown-3, trinuclear clusters. Its ability to complex with metal ions allows for the formation of stable and unique metal complexes with potential applications in various fields.
Used in Coordination Chemistry:
In coordination chemistry, Phenyl 2-pyridyl ketoxime is used as a ligand for the formation of metal complexes. Its complexation reaction with metal ions has been studied potentiometrically, providing insights into the stability and properties of the resulting complexes.
Used in Analytical Chemistry:
The complexation properties of Phenyl 2-pyridyl ketoxime can be utilized in analytical chemistry for the selective detection and quantification of metal ions. Its ability to form stable complexes with specific metal ions can be exploited in the development of sensors and analytical methods.
Used in Material Science:
The metal complexes formed using Phenyl 2-pyridyl ketoxime can be employed in material science for the development of new materials with unique properties. These materials can be used in various applications, such as catalysts, electronic devices, and advanced materials with tailored properties.

Purification Methods

The E-isomer crystallises from EtOH (charcoal). It isomerizes to the Z-isomer on melting or in boiling o-xylene, and crystallises from EtOH or cyclohexanol with m 166-168o. [Beilstein 21 H 330, 21 III/IV 4120, 21/8 V 568.]

InChI:InChI=1/C12H10N2O/c15-14-12(10-6-2-1-3-7-10)11-8-4-5-9-13-11/h1-9,15H/b14-12-

Upstream product

• 91-02-1 phenyl(pyridin-2-yl)methanone 

Downstream Products

• 413579-18-7 Os3H(CO)11(η(2)-ON=CPh(NC5H4)2) 
• 413579-17-6 Os3(CO)8(μ-η(3)-ON=CPh(NC5H4))2 
• 413579-19-8 Os3(μ-H)(CO)9(μ-η(3)-ON=CPh(NC5H4)) 
• 952505-03-2 [(1,4,7-trimethyl-1,4,7-triazacyclononane)Ni(PyA-Ph)3Ni]ClO₄ 
• 39930-11-5 1-phenyl-1-(pyridin-2-yl)methanamine 
• 1211004-20-4 [Cu₂(phenyl 2-pyridyl ketone oxime^(1-))2(hexafluoroacetylacetonate)2] 

Relevant academic research and scientific papers

A Pentanuclear Cobalt Complex with two [CoII(CH3O)3]– Units Wrapping a Triangular [CoIII3O]7+ Core: Synthesis, Structure, and Magnetic Properties

The reaction of Hppko (Hppko = phenyl 2-pyridyl ketone oxime) and CoCl2·6H2O in the CH3OH solvent with the presence of triethylamine (NEt3) at room temperature and the exposure to air resulted in the formation of a new pentanuclear, mixed-valence cobalt complex with the molecular formula [{CoII(CH3O)3}2{CoIII3(μ3-O)(ppko)3}Cl2]. X-ray single crystal analysis displays a trigonal bipyramid configuration with the terminal two CoII ions wrapping an triangle [CoIII3O]7+ core. The intermolecular C–H···O and C–H···Cl interactions form a 2D network framework. The analysis of magnetic susceptibility revealed the dominant antiferromagnetic interactions and strong orbital contribution of CoII ions.

Construction and regulation of imidazo[1,5-a]pyridines with AIE characteristics via iodine mediated Csp2?H or Csp?H amination

The widespread applications of aggregation-induced emission luminogens (AIEgens) inspire the creation of AIEgens with novel structures and functionalities. In this work, we focused on the direct and efficient synthesis of a new type of AIEgens, imidazo[1,5-a]pyridicne derivatives, via iodine mediated cascade oxidative Csp2–H or Csp–H amination route from phenylacetylene or styrenes under mild conditions. The resulted compounds showed excellent AIE characteristics with tunable maximum emissions, attractive bioimaging performance, and potential anti-inflammatory activity, which exert broad application prospects in material, biology, medicine, and other relevant areas.

Tertiary α-diarylmethylamines derived from diarylketimines and organomagnesium reagents

Organomagnesium reagents enable swift and versatile derivatisation of diarylimines to the corresponding α-substituted diarylmethylamines in excellent yields, through fast and clean reactions. Where it occurs, 1,2-reduction can be circumvented using readily accessible dialkylmagnesium reagents. This journal is

Effective conversion of heteroaromatic ketones into primary amines via hydrogenation of intermediate ketoximes

A process to access heteroaromatic primary amines from the corresponding heteroaromatic ketones has been developed. A broad range of previously reported methods to convert ketones to primary amines was examined on heterocyclic ketones without success, including Leuckart-Wallach conditions, borane reductions, and transition-metal-catalyzed hydrogenations. Unique among the catalysts examined, Raney cobalt produced the desired primary heterocyclic amine. Raney cobalt hydrogenation of structurally varied heterocyclic ketoximes was demonstrated to form primary amines in good selectivity under mild conditions, and the products are easily isolated in high yield. Additionally, this is the first report of a systematic evaluation of the capabilities of Raney cobalt as an oxime hydrogenation catalyst.

Synthesis, docking study and β-Adrenoceptor activity of some new oxime ether derivatives

A new series of oxime ethers 4a-z was designed and synthesized to test the blocking activity against β1 and β2-Adrenergic receptors. Docking of these ether derivatives into the active site of the identified 3D structures of β1 and β2-Adrenergic receptors

Molecular structures of dinuclear zinc(II) complexes of chiral tridentate imine and amine ligands: Effect of ligand geometry on diastereoselectivity

Racemic mixtures of Schiff bases (L1H and L2H) were reduced to respective amines (L1′H and L2′H). Compounds of composition [Zn 2(L1)2(NCO)2] (1), [Zn(L1)N3] n (2), [Zn2(L2)2(NCO)2] (3), [Zn2(L1′)2(NCO)2] (1′), [Zn 2(L1)2(N3)2]·2DMF (2′·2DMF) and [Zn2(L2′)2(NCO) 2]·DMF (3′·DMF) were synthesized using these ligands, Zn(NO3)2·6H2O and NCO - or N3- ions. Molecular structures of all six compounds have been established. Both imine and amine ligands have N 2O donor set, but coordinate, respectively, in meridional and facial fashions. First four complexes are monochelates and last two are bis-chelates. The Zn2O2 unit in 1-3 has RS combination of imine where as in 1′ has RR(SS) combinations of amine. In 2′ and 3′, zinc(II) bis-chelates have cis,cis,trans-(OP)2(N A)2(NY)2 stereochemistry and cis-(OP)2 disposition further coordinate to tetrahedral zinc. Compound 1′ exhibits 1D hydrogen-bonded polymer by enantioselective H-bonding interaction. In 2′, DMF molecules assemble RR and SS bis-chelates through N-H?O interactions.

Diastereoselectivity in dinuclear complexes of chiral tridentate ligands

Using a racemic mixture of two chiral tridentate ligands 2-((1-(2-pyridyl)ethylimino)methyl)phenolate ion (L1) and 2-((phenyl(2-pyridyl) methylimino)methyl)phenolate ion (L2) and Cu(II) or Ni(II) salts, complexes having formulae [Cu(L2)(μ-1,1-NO3)]2 (1), [Cu(L2)(μ-Cl)]2 (2), [Cu2(L2)2(μ-1,2- SO4)] (3), [Cu2(L1)2(μ-1,2-SO4)] (4) and [Ni2(L2)2(OAc)(N(CN)2)(MeOH)] (5) were synthesized and characterized. Determination of molecular structures of all the five complexes confirmed the presence of a dimetallic core constructed by monochelates of the ligands. Compound 1, 2 have NO3- and Cl- bridge between two copper centers and 3-5 have phenoxo as well as SO42- (3,4) and OAc- (5) bridges. Compounds 1 and 2 have center of inversion in the dicopper core and are heterochiral. Whereas, in 3-5 center of inversion do not lie in the dimetallic core and are homochiral. Compound 1 has a rare feature of μ-1,1-NO3- bridge between two copper centers.

Coordination behavior of the (diphenylphosphanyl)[α-(2-pyridyl) benzyl]amide anion toward lithium and zinc cations

A two-step synthesis allows the preparation of [α-(2-pyridyl)benzyl] amine (1) in good yield. Phosphanylation in the presence of triethylamine gives (diphenylphosphanyl)[α-(2-pyridyl)benzyljamine (2), which crystallizes as a racemate in the centrosymmetric triclinic space group P1. The P-N bond lengths exhibit an average value of 168.3 pm. Lithiation of 2 with n-butyllithium yields dimeric semi(tetrahydrofuran)lithium (diphenylphosphanyl)[α-(2- pyridyl)benzyl]amide (3) with the lithium atoms in different environments. One Li atom, is in a distorted, tetrahedral environment and the other in a trigonal-planar coordination sphere with bridging amide moieties (av. Li-N 201.8, Li-O 192.4 pm). Zincation of 2 with dimethylzinc leads to the formation of dimeric methylzinc (diphenylphosphanyl)[α-(2-pyridyl)benzyr]amide (4) with a central six-membered (ZnNP)2 ring in a boat conformation (av. Zn-N 201.8, Zn-P 245.9 pm). The endocyclic P-N bonds are rather short (av. value 162.7 pm).

Synthesis of fluorescent 1,3-diarylated imidazo[1,5-α]pyridines: Oxidative condensation-cyclization of aryl-2-pyridylmethylamines and aldehydes with elemental sulfur as an oxidant

Oxidative condensation - cyclization of aldehydes and aryl-2- pyridylmethylamines proceeded in the presence of a stoichiometric amount of elemental sulfur as an oxidant in the absence of catalyst. The reaction gave a variety of 1,3-diarylated imidazo[l,5-a]pyridines in good to high yields. The products showed fluorescence emission in a wavelength range of 454-524 nm. The quantum yields of 1,3-diarylated imidazopyridines were greatly improved compared to those of the parent 3-monosubstituted compounds.

O-Vinyldiaryl- and O-vinylaryl(hetaryl)ketoximes: A breakthrough in O-vinyloxime chemistry

O-Vinyldiarylketoximes and O-vinylaryl(hetaryl)ketoximes, a novel family of stable O-vinyloximes, are synthesized by a straightforward, unusually fast vinylation of diarylketoximes and aryl(hetaryl)ketoximes with acetylene in a superbase system of KOH-DMSO (60-80°C, 5-7min). Yields of up to 90% were obtained, thus introducing into organic synthesis a new group of highly promising building blocks and monomers.