159150-90-0

Upstream product

• 192819-69-5 3-[(bis-(pyridin-2-yl-methyl)amino)-methyl]-2-hydroxy-5-methyl-benzaldehyde 
• 159150-89-7 8-(bis(2-pyridylmethyl)aminomethyl)-6-methyl-2-phenyl-2,4-dihydro-1,3-benzodioxine 
• 65448-72-8 2-hydroxy-3-(hydroxymethyl)-5-methylbenzaldehyde 
• 1539-42-0 bis[(2-pyridyl)methyl]amine 
• 159150-88-6 8-(bromomethyl)-6-methyl-2-phenyl-2,4-dihydro-1,3-benzodioxine 
• 159150-87-5 (6-methyl-2-phenyl-2,4-dihydro-1,3-benzodioxin-8-yl)methanol 
• 91-04-3 2,6-bis(hydroxymethyl)-4-methylphenol 
• 192819-68-4 3-chloromethyl-5-methylsalicylaldehyde 

Downstream Products

• 1450852-60-4 C₃₄H₃₆N₆OS 
• 177034-90-1 2-([bis(2-hydroxybenzyl)amino]methyl)-6-([bis(2-pyridinylmethyl)amino]methyl)-4-methylphenol 
• 170659-81-1 2-[[bis(2-pyridinomethyl)amino]methyl]-6-[[[(2-hydroxyphenyl)methyl](2-pyridinylmethyl)amino]methyl]-4-methylphenol 
• 156214-73-2 2-(N,N-bis(2-methylpyridyl)aminomethyl)-6-(N-(2-hydroxyphenyl)-N-(2-pyridylmethyl)aminomethyl)-4-methylphenol 

Relevant academic research and scientific papers

Deprotonation in Mixed-Valent Diiron(II,III) Complexes with Aniline or Benzimidazole Ligands

We have previously investigated cis/trans isomerization processes in phenoxido-bridged mixed-valent FeIIFeIII complexes that contain either one aniline or one anilide ligand. In this work, we compare the properties of similar complexes bearing one terminal protic ligand, either aniline or 1H-benzimidazole. Whatever the ligand, 1H NMR spectroscopy clearly evidences that the complexes are present in CH3CN as a mixture of cis- and trans-isomers in a close to 1:1 ratio. We show here that addition of NEt3 indeed allows the deprotonation of these ligands, the resulting complexes bearing either anilide or benzimidazolide that are coordinated to the ferric site. The latter are singular examples of a high-spin ferric ion coordinated to a benzimidazolide ligand. Whereas the trans-isomer of the anilide complex is the overwhelming species, benzimidazolide species are mixtures of cis- and trans-isomers in equal proportions. Moreover, cyclic voltammametry studies show that FeIIIFeIII complexes with 1H-benzimidazole are more stable than their aniline counterparts, whereas the reverse is observed for the deprotonated species. (Graph Presented).

Trinuclear CuII complex containing a new pentadentate ligand: Structure, magnetism, physicochemical properties and catecholase activity

A new pentadentate ligand, 2-N-((bis(pyridin-2-ylmethyl)amino)methyl)-6-(methoxymethyl)-4-methylphenol (BPM3F), was synthesized and used to obtain a trinuclear copper(II) complex, [Cu3(BPM3F)2(μ-OAc)2](ClO4)sub

Effect of coordination dissymmetry on the catalytic activity of manganese catalase mimics

Two mixed-valence Mn(II)Mn(III) complexes, [Mn2L1(OAc)2(H2O)]BPh4·2.5H2O and [Mn2L2(OAc)2]·4H2O, obtained with unsymmetrical N4O2

Catalytic Oxidation of Alkanes and Alkenes by H2O2 with a μ-Oxido Diiron(III) Complex as Catalyst/Catalyst Precursor

A new μ-oxo diiron(III) complex of the lithium salt of the pyridine-based unsymmetrical ligand 3-[(3-{[bis(pyridin-2-ylmethyl)amino]methyl}-2-hydroxy-5-methylbenzyl)(pyridin-2-ylmethyl)amino]propanoate (LiDPCPMPP), [Fe2(μ-O)(LiDPCPMPP)2](ClO4)2, has been synthesized and characterized. The ability of the complex to catalyze oxidation of several alkanes and alkenes has been investigated by using CH3COOH/H2O2 (1:1) as an oxidative system. Moderate activity in cyclohexane oxidation (TOF = 33 h-1) and good activity in cyclohexene oxidation (TOF = 72 h-1) were detected. Partial retention of configuration (RC = 53%) in cis- and trans-1,2-dimethylcyclohexane oxidation, moderate 3/2 selectivity (4.1) in adamantane oxidation, and the observation of a relatively high kinetic isotope effect for cyclohexane oxidation (KIE = 3.27) suggest partial metal-based oxidation, probably in tandem with free-radical oxidation. Low-temperature UV/Vis spectroscopy and mass spectrometric studies in the rapid positive detection mode indicate the formation of a transient peroxido species, [Fe2(O)(O2)(LiDPCPMPP)2]2+, which might be an intermediate in the metal-based component of the oxidation process. A μ-oxido diiron(III) complex, [Fe2(μ-O)(LiDPCPMPP)2](ClO4)2, was synthesized and characterized. This complex was used as catalyst in C-H bond oxidation with CH3COOH-H2O2 as chemical oxidant. Reactivity studies indicate that the oxidation process goes through a metal-based mechanism concomitant with a radical process.

Changes in magnetic properties from solid state to solution in a trinuclear linear copper(II) complex

A linear trinuclear copper(ii) complex containing phenoxido- and alkoxido-bridges between the metal centers has been isolated and structurally characterized. The complex cation consists of a linear array of three copper ions, assembled by means of two dou

Synthesis, structural, magnetic, and redox properties of asymmetric diiron complexes with a single terminally bound phenolate ligand. Relevance to the purple acid phosphatase enzymes

New asymmetrical ligands (H2L) have been synthesized to provide both a bridging and a terminal phenolate to a pair of iron ions in order to mimic the binding of a single terminal tyrosinate at the diiron center of the purple acid phosphatases. H2L1 is 2-(bis(2-pyridylmethyl) amino)methyl]-6-[((2-pyridylmethyl)(2-phenol)amino)methyl] 4-methylphenol and H2L'1 and H2L2 are obtained by replacing the 2-phenol group by the 5-nitro-2-phenol and the 6-methyl-2-phenol residues, respectively. A series of mixed valence diiron complexes [Fe(II)Fe(III)L(X)2](Y) have been obtained where (X)2 is the dianion of m-phenylenedipropionate or (H2PO4)2 and Y = BPh4 or PF6 (L = L1, 1a (X)2 = mpdp, Y = BPh4, 1b: (X)2 = (OAc)2, Y = BPh4, 1c: (X)2 = (OBz)2, Y = BPh4, 1d: (X)2 = (H2PO4)2 Y = PF6; L = L'1: 1'a(X)2 mpdp, Y = BPh4; L = L2: 2c: (X)2 = (OBz)2, Y = BPh4, 2d: (X)2 (H2PO4)2, Y = PF6. Diferric complexes have been obtained also either by direct synthesis or by iodine oxidation of the mixed valence precursor (L = L1, 3a (X)2 = mpdp, Y = BPh4, 3d: (X)2 = (H2PO4)2, Y = PF6; L = L2, 4d: (X)2 = (H2PO4)2, Y = PF6. Complex 1a [Fe(II)Fe(III)L(mpdp)](BPh4)) has been characterized by X-ray diffraction techniques. 1a crystallizes in the monoclinic space group P21/a with the following unit cell parameters: a = 22.038 (9) ?, b = 16.195 (8) ?, c = 16.536 (7) ?, β = 97.26 (1)°, Z = 4. The significant differences in the Fe-O bond lengths indicate that the metal centers are ordered. The complexes have been studied by electronic spectral, resonance Raman, magnetic susceptibility, Mossbauer, NMR, and electrochemical techniques. Mossbauer and NMR spectroscopies concur to probe that the valences of the mixed valence compounds are trapped in solution as well as in the solid state at room temperature. The electronic spectrum of the mixed-valence compounds are dominated by a charge transfer transition in the 400-600 nm domain which moves to the 550-660 nm range upon oxidation to the diferric state. In addition they exhibit a weak and broad intervalence transition close to 1100 nm. Electrochemical studies show that the systems exist in the three redox states Fe(II)Fe(II)/Fe(II)Fe(III)/Fe(III)Fe(III). Moreover they show that the introduction of the terminal phenol group results in a thermodynamic destabilization of the diferrous state higher than the stabilization of the diferric state. An expanded stability domain of the mixed valence state is therefore observed which is probably due mostly to the asymmetry of the compounds. In addition a chemical destabilization of the reduced state of 1a, 1c, and 1'a is observed. Comparison of the carboxylate and phosphate derivatives leads to attribute it to the partial dissociation in solution of the carboxylate oxygen trans to the phenolate. The latter feature bears an intrinsic resemblance with the dissociation of iron which is observed when purple acid phosphatases are reduced by dithionite. These studies clearly show the importance of tyrosine binding on the redox properties of the PAP enzymes. This questions the relationship of such a redox specificity with a hydrolytic function and raises the possibility that the latter may be redox regulated or that another (redox based) function is actually involved, possibly in line with the ability of the enzymes to react with peroxides.

A versatile key synthon for the syntheses of ligands potentially suited for the preparation of μ-phenoxo dimetallic complexes with two non equivalent complexation sites

The synthon S, easily prepared in two steps (65% yield) from 2,6-bis(hydroxymethyl)-4-methylphenol, may allow the syntheses of various dinucleating ligands bearing two chemically different coordination environments. The preparation of the dinucleating lig