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Usage

Uses

Used in Pharmaceutical Industry:
2-([(4-Chlorophenyl)imino]methyl)phenol is used as a key intermediate in the synthesis of various pharmaceutical products. Its unique chemical structure allows it to be incorporated into the development of new drugs, potentially offering novel therapeutic options for a range of medical conditions.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 2-([(4-Chlorophenyl)imino]methyl)phenol plays a vital role in the creation of a variety of organic compounds. Its reactivity and functional groups enable chemists to use it as a building block for synthesizing complex molecules with diverse applications in various fields, including materials science, agrochemicals, and specialty chemicals.

InChI:InChI=1/C13H10ClNO/c14-11-5-7-12(8-6-11)15-9-10-3-1-2-4-13(10)16/h1-9,15H

Upstream product

• 106-47-8 4-chloro-aniline 
• 90-02-8 salicylaldehyde 
• 19865-61-3 N-(salicylidene)-4-chlorophenylamine-N-oxide 
• 89-95-2 2-methyl-benzyl alcohol 
• 53745-07-6 6-[1-(4-Chloro-phenylamino)-meth-(Z)-ylidene]-cyclohexa-2,4-dienone 

Downstream Products

• 33877-81-5 3-(4-chloro-phenyl)-3,4-dihydro-2H-benzo[e][1,3,2]oxazaborinine 
• 81824-94-4 3-(4-Chloro-phenyl)-2-[(E)-2-(2-hydroxy-phenyl)-vinyl]-3H-quinazolin-4-one 
• 7193-94-4 2-((4-chlorophenylamino)methyl)phenol 
• 89-95-2 2-methyl-benzyl alcohol 
• 51892-07-0 3-(4-chlorophenyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine 
• 116334-59-9 bis(N-(p-chlorophenyl)salicylaldiminato)(1,10-phenanthroline)zinc(II) 
• 16985-34-5 bis(2-{(E)-[(4-chlorophenyl)imino]methyl}phenolate)zinc(II) 
• 32065-25-1 bis{N-(4-chlorophenyl)salicylideneaminato}oxovanadium(IV) 
• 28548-10-9 {PbCl₂(C₁₃H₉ClNO)2} 
• 108151-43-5 tris(salicylidene-4-chloro-anilinato)-cobalt(III) 
• 97982-50-8 C₆H₅AsO₃^(2-)*Al⁽³⁺⁾*C₆H₄ClNCHC₆H₄O^(1-) = C₆H₅AsO₃Al(OC₆H₄CHNC₆H₄Cl) 
• 98003-04-4 (CH₃)3SiOAl(OC₆H₄CHNC₆H₄Cl)2 
• 152600-19-6 {Ru(P(C₆H₅)3)2(C₆H₄(O)CHN(C₆H₄(Cl)))2} 
• 141823-33-8 (((CH₃)2CHC₆H₄CH₃)RuCl(OC₆H₄CHNC₆H₄Cl)) 

Relevant academic research and scientific papers

Structure and characterization of bis(N-p-chloro-phenyl-salicylideneaminate) Schiff base copper(II) complex: Cu[N-p-Cl-Ph-Sal]2

The crystal and molecular structure of the title compound has been determined by X-ray crystallography. It crystallizes in the monoclinic system, space group P21/c, with lattice parameters a = 13.678(3), b = 10.729(2), c = 8.1996(2) A, β= 98.96°, V = 1188.7(4) A 3, and Z = 4. The crystal structure contains two centrosymmetric molecules of bis (N-p-chloro-phenyl-salicylideneaminate) Schiff base copper(II). Copper(II) ion is coordinated in a slightly distorted trans square-planar configuration, the distortion consisting of a reduction of the N-Cu-O angle with the chelate rings from the ideal value of 90°. The p-chlorophenyl rings with salicylidene moieties form a dihedral angle of 38.96°.

Nonlinear optical properties of some derivatives of salicylaldimine-based ligands

A series of potential nonlinear optical (NLO) compounds, (-OH) and (-Cl) substituted derivatives of salicylaldimine-based ligands 1-6 (Fig. 2), was designed and synthesized. Compounds 1 and 2 were characterized by X-ray diffraction analysis, elemental analysis, IR, 1H-NMR, 13C-NMR and UV-Visible spectroscopies. The electric dipole moments (μ) and the first hyperpolarizabilities (β) of the compounds 1-6 were calculated using ab-initio quantum calculations (finite field M?ller Plesset perturbation theory). The calculation results reveal that the substituent positions play a significant role in NLO properties of these compounds.

Facile synthesis, solublization studies and anti-inflammatory activity of amorphous zinc(Ii) centered aldimine complexes

In this study, Zn(II) centered complexes with aldimine derivatives were synthesized using green solvent, polyethylene glycol (PEG-400) and amorphous complexes were characterized by FT-IR, multinuclear (1H and13C NMR), elemental and thermal analysis. Thermogravimetric analysis indicated the extended thermal stability of the synthesized complexes. All the Zn(II) complexes show very significant photoexcitation in the range of 318 – 384 nm and photoemission in the range of 502 – 562 nm. Among all the complexes, Zn(II) complex (3Zn) showed minimum band gap value, 2.35 eV. These amorphous complexes have been reported for their wide applications in biomedical sciences. The synthesized aldimine ligands and Zn(II) complexes were investigated for anti-inflammatory activity and these complexes showed more anti-inflammatory potential than the corresponding aldimine ligands. The solubilization of zinc complexes in sodium dodecyl sulphate was also investigated to reveal the interaction of metal complexes by using UV-Visible spectroscopy and electrical conductivity measurements.

Influence of substituents on the structure of Schiff bases Cu(II) complexes

The relationship between molecular conformation and substituent effects of salicylaldehyde Schiff-base Cu(II) complexes was explored. For this study, eight samples of the complexes Cu(Sal-X)2 (X = OMe, Me, H, F, Cl, Br, CF3 and CN) w

Ru(III) complexes of phenoxy-imine ligands: Synthesis, characterisation and testing as oxidation catalysts

Summary: A series of new mononuclear Ru(III) complexes bearing phenoxy-imine Schiff base tetradentate ligands (phenylimino, 4-chlore phenylimino, 3,4-dichlore phenylimino) have been prepared and characterized by elemental analysis, TGA, UV-VIS, FT-IR, 1H-NMR and 13C NMR spectra. The proposed structure of the ligands have a O2N2 core to form mononuclear Ru (III) complexes. Preliminary studies on the catalytic performances of the compounds in the cycloalkane oxydation are described. The catalytic effect of all Ru complexes results in the epoxidation reaction of cyclohexane, as shown in the substrate conversion reaction appears to be very high.

Synthesis, spectroscopic characterization and computational studies of Schiff base complexes of tin(IV) chloride

Reaction of anhydrous tin(IV) chloride with mono functional bidentate Schiff bases (sbnH), in 1:2 molar ratios, gives complexes of the type, [(sbn)2SnCl2] (1-4) (where, n=1-4; sb=2-(((4-chlorophenyl)imino)methyl

Effect of substituents on the UV spectra of supermolecular system: Silver nanoparticles with bi-aryl Schiff bases containing hydroxyl

Effect of substituents on the ultraviolet (UV) spectra of supermolecular system involving silver nanoparticles (AgNPs) and Schiff bases was investigated. AgNPs and 49 samples of model compounds (MC), bi-aryl Schiff bases containing hydroxyl (XBAY, involving 4-OHArCH?NArY, 2-OHArCH?NArY, XArCH?NAr-4′-OH, and XArCH?NAr-2′-OH), were synthesized. The size of AgNPs was characterized by transmission electron microscopy (TEM), and the UV absorption spectra of AgNPs, XBAYs, and MC-AgNPs mixed solutions were measured, respectively. The results show that (1) the size of AgNPs is larger in MC-AgNPs solutions than that in AgNPs solution due to the distribution of MC molecules on the surface of AgNPs; (2) the UV absorption wavelength of XBAYs changes in the action of AgNPs and their wavelength shift exists limitation between XBAY and MC-AgNPs solutions; and (3) the wavelength shift limit of MC-AgNPs (λWSL) is influenced by the substituents X and Y and the position of hydroxyl OH. The wavenumber ΔνWSL of λWSL can be quantified by employing the excited-state substituent constant σexCC and Hammett constant σ of substituents X and Y. Comparing with the 4-OH, the 4′-OH makes the ΔνWSL a red shift, whereas the 2′-OH, comparing with the 2-OH, makes the ΔνWSL a blue shift.

Syntheses, structures and catalytic properties of ruthenium(II) nitrosyl complexes with bidentate and tetradentate Schiff base ligands

Treatment of Ru(NO)Cl3·xH2O with 1 equiv. bidentate Schiff bases in the presence of triethylamine in DMF/THF afforded a series of anionic ruthenium(II) nitrosyl complexes of the type [Et3NH][Ru(κ2-N,O-LR)(NO)Cl3] (HLR = 2-butyliminomethyl-phenol 1, 2-(benzylimino-methyl)-phenol 2, 2-[(4-chloro-phenylimino)-methyl]-phenol 3, 2-[(4-nitro-phenylimino)-methyl]-phenol 4, 2-[(2,6-diisopropyl-phenylimino)-methyl]-phenol 5). Interaction of Ru(NO)Cl3·xH2O and 1 equiv. tetradentate Schiff bases under the same condition led to isolation of an anionic complex [Et3NH][Ru(κ2-N,O-L-CH2CH2-NOH)-(NO)Cl3] (HL-CH2CH2-NOH = N,N′-disalicylidene-1,2-ethanediamine 6) and a neutral complex [Ru(salen-phn)(NO)Cl] (H2salen-phn = N,N′-disalicylidene-1,2-phenyldiamine 7). The molecular structures of 1·?C2H5OH, 2–6, and 7·CH2Cl2 have been determined by single-crystal X-ray crystallography. Investigation of the catalytic properties of ruthenium(II) nitrosyl complexes 1–7 showed that they are efficient catalytic precursors for the transfer hydrogenation of acetophenone.

Synthesis, spectral studies and DFT calculation of copper(II) complexes with mixed ligands

The reaction of copper(II) chloride with Schiff bases and alkanolamines in 1:1:1 molar ratio(s) resulted a series of mixed ligand copper(II) complexes of general formula [Cu(sb)(aa)] (1-6), [where sb = Schiff base; salicylidine-1-aminobenzene (sabH) (1,4)

Carbocation Organocatalysis in Interrupted Povarov Reactions to cis-Fused Pyrano- and Furanobenzodihydropyrans

Tritylium cation-catalyzed interrupted Povarov reactions afforded cis-4-aminobenzodihydropyrans in excellent yields (90 %) within 10 min by low catalyst loadings (1 mol-%). A mechanism involving Lewis acidic catalysis by a carbocation was proposed and val