3099-28-3

Usage

Uses

Used in Chemical Synthesis:
2,6-Bis(chloromethyl)pyridine is used as a building block for the synthesis of various pyridine derivatives, which are important in the development of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Synthesis of Fluorescent Chemosensors:
2,6-Bis(chloromethyl)pyridine is used as a receptor in the synthesis of a sensitive fluorescent chemosensor for Hg2+, composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine.
Used in Preparation of Carbene Pincer Ligands:
2,6-Bis(chloromethyl)pyridine is used in the preparation of carbene pincer ligands, which are required for the preparation of palladium pincer carbene complexes. These complexes are important in catalysis and other chemical reactions.
Used in Synthesis of PNN Ligands:
2,6-Bis(chloromethyl)pyridine is used in the synthesis of 2-(di-tert-butylphosphinomethyl)-6-diethylaminomethyl)pyridine, a PNN ligand. This ligand is useful in the development of transition metal complexes for various applications, such as catalysis and coordination chemistry.

Upstream product

• 1195-59-1 2.6-bis(hydroxymethyl)pyridine 
• 108-48-5 2,6-dimethylpyridine 
• 134536-79-1 {2,6-bis(chloromethyl)pyridine}trichlorogold(III) 
• 16887-00-6 chloride 
• 15658-60-3 diethyl-2,6-pyridinedicarbonyl ester 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 

Downstream Products

• 123434-53-7 2,6,10-tritosyl-2,6,10-triaza<11>(2,6)pyridinofane 
• 136670-16-1 2,6-di-(2'-nitro-4'-formylphenoxymethyl)pyridine 
• 123434-50-4 2,8-dibenzenosulfonyl-2,8-diaza<9>(2,6)pyridinofane 
• 98572-18-0 3,11-ditosyl-3,11,17,18-tetraazatricyclo<11.3.1^5,9>octadeca-1(17),5(18),6,8,13,15-hexaene 
• 115078-42-7 N,N',N''-tri-p-tosyl-2,11,20-triaza<3.3.3>(2,6)pyridinophane 
• 66433-95-2 2,6-Bis(2-formylphenoxymethyl)pyridine 
• 144106-20-7 2,6-bis(4-formylphenoxymethyl)pyridine 
• 144106-21-8 C₂₃H₂₁NO₆ 
• 136694-85-4 2,5-di<2'-nitro-4'-(10,15,20-triphenyl-5-porphyrinyl)phenyl>oxymethylpyridine 
• 131443-56-6 5-<3'-nitro-4'-(6''-chloromethyl-2''-methyleneoxypyridyl)phenyl>-10,15,20-triphenylporphyrin 
• 66433-99-6 2,6-bis(2-methoxyphenoxymethyl)pyridine 
• 123434-51-5 2,9-ditosyl-5-oxa-2,9-diaza<10>(2,6)pyridinofane 

Relevant academic research and scientific papers

A comparative study of magnetization dynamics in dinuclear dysprosium complexes featuring bridging chloride or trifluoromethanesulfonate ligands

We utilized a rigid ligand platform PyCp22- (PyCp22- = [2,6-(CH2C5H3)2C5H3N]2-) to isolate dinuclear Dy3+ complexes [(PyCp2)Dy-(μ-O2SOCF3)]2 (1) and [(PyCp2)Dy-(μ-Cl)]2 (3) as well as the mononuclear complex (PyCp2)Dy(OSO2CF3)(thf) (2). Compounds 1 and 2 are the first examples of organometallic Dy3+ complexes featuring triflate binding. The isolation of compounds 1 and 3 allows us to comparatively evaluate the effects of the bridging anions on the magnetization dynamics of the dinuclear systems. Our investigations show that although the exchange coupling interactions differ for 1 and 3, the dynamic magnetic properties are dominated by relaxation via the first excited state Kramers doublet of the individual Dy sites. Compounds 1 and 3 exhibit barriers to magnetization reversal (Ueff = 49 cm-1) that can be favorably compared to those of the previously reported examples of [Cp2Dy(μ-Cl)]2 (Ueff = 26 cm-1) and [Cp2Dy(thf)(μ-Cl)]2 (Ueff = 34 cm-1).

Synthesis, spectroscopy, and crystal structure of a new stable biscyclopentadienyl uranium(IV) dichloride containing two C5H4-rings interlinked by a metal-coordinated 2,6-bis(methylene)pyridyl unit

Reaction of the new disodium salt: Na2IVCl2-derivative (Cp = η5-C5H5): μ-(η5-C5H4)2UIVCl2 (1).According to a single-crystal X-ray study, 1 involves a notably strong U-N bond (U-Nav: 2.62(1) Angstroem) along with two nonequivalent Cl ligands (U-Cl: 2.615(3) and 2.636(3) Angstroem).The low-temperature 1H NMR spectrum of the paramagnetic complex is in full accord with the solid state structure 1.Up to room temperature, the dissolved molecules of 1 show no fluxionality on the NMR time scale, although the two CH2 proton resonances appear to undergo coalescence.

Cobalt complexes of an OSNSO-tetrapodal pentadentate ligand: Synthesis, structures and reactivity

The novel pentadentate tetrapodal proligand 2,6-bis[(2-hydroxyphenyl)sulfanylmethyl]pyridine (1·H2) and its cobalt(II) complex [Co(1)] (2) were synthesized and characterized by several analytical (EA, ESI-MS) and spectroscopic methods (NMR or EPR, FT-IR), including X-ray crystallography for 1·H2. Cyclic voltammetry studies showed that 2 undergoes a reversible metal-based oxidation (CoII/CoIII). Complex 2 was designed to be applied to organometallic mediated radical polymerization (OMRP), however it exhibited an extremely poor solubility in non-coordinating solvents and several vinyl monomers (styrene, vinyl acetate and tert-butyl acrylate), which hampers its potential as moderator. Complex 2 has a high affinity towards Lewis bases, such as pyridine, leading to the clean formation of the mono-pyridine adduct 2·py, as confirmed by X-ray crystallography. In 2·py, ligand 1 is pentacoordinated to the CoII center, with the two thioether-phenolate (S,O) moieties oriented anti to each other, and the only free coordination site of the octahedron is completed by the additional pyridine, trans to the central pyridine linker of 1. The equilibrium between 2 and 2·py could be studied by 1H NMR. Complex 2 could be cleanly and quantitatively oxidized to its diamagnetic iodo cobalt(III) analog [Co(1)I] (3), by simple reaction with iodine. The latter could then be subjected to a halide abstraction reaction, mediated by K[B(C6F5)], affording the cationic complex [Co(1)][B(C6F5)], 4.

Metal-ion Selectivity by Macrocyclic Ligands. Part 1. The Interaction of NiII and CuII with Pyridinyl-derived N3O2 Macrocycles; The X-Ray Structures of a Free Macrocycle, its Endomacrocyclic Complexes of NiII and CuII and an Exomacrocyclic Nickel(II) Complex

The interaction of CuII and NiII with two macrocycles L1 and L2, each containing an N3O2 donor set, has been investigated.Spectrophotometric studies in dimethyl sulphoxide reveal the formation of complexes with 1:1 and 1:2 metal:ligand ratios and conductometric studies in the same solvent indicated that all of the complexes were 1:2 electrolytes.Conductometric titration of the 1:1 copper(II) complexes with chloride in each case indicated the formation of a 1:1 electrolyte, presumably through co-ordination of a chloride ion to the central copper of each complex.Similar titration of the nickel(II) complexes gave evidence for the formation of dinuclear species; each of these was postulated to contain a bridging chloride anion.The stability constants of the complexes together with their enthalpies of co-ordination have been determined in 95percent methanol.Extraction and related transport experiments were carried out and under the conditions employed CuII was favoured over NiII.The X-ray crystal structures of the free macrocycle L1, the 1:1 complexes 1(H2O)>2 and 1(I)>I*MeOH, and the 1:2 complex 12(NO3)>NO3*2MeOH have been determined.The metal in 1(H2O)>2 is six-co-ordinate and lies within the folded macrocyclic cavity.The donor set comprises the five macrocyclic donor atoms and a water molecule.Overall, the co-ordination sphere corresponds to a restricted tetragonal rhombic arrangement.The complex 1(I)>*MeOH also has all donors of the macrocycle co-ordinated with an iodide anion occupying the sixth site to yield a distorted-octahedral geometry.The structure of 12(NO3)>NO3*2MeOH shows that the nickel is again six-co-ordinated, to the aliphatic nitrogen atoms from two macrocycles (each showing exo co-ordination) and a bidentate nitrate anion.

Steric Effect on the Nucleophilic Reactivity of Nickel(III) Peroxo Complexes

A set of nickel(III) peroxo complexes bearing tetraazamacrocyclic ligands, [NiIII(TBDAP)(O2)]+ (TBDAP = N,N′-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane) and [NiIII(CHDAP)(O2)]+ (CHDAP = N,N′-dicyclohexyl-2,11-diaza[3.3](2,6)pyridinophane), were prepared by reacting [NiII(TBDAP)(NO3)(H2O)]+ and [NiII(CHDAP)(NO3)]+, respectively, with H2O2 in the presence of triethylamine. The mononuclear nickel(III) peroxo complexes were fully characterized by various physicochemical methods, such as UV-vis, electrospray ionization mass spectrometry, resonance Raman, electron paramagnetic resonance, and X-ray analysis. The spectroscopic and structural characterization clearly shows that the NiO2 cores are almost identical where the peroxo ligand is bound in a side-on fashion. However, the different steric properties of the supporting ligands were confirmed by X-ray crystallography, where the CHDAP ligand gives enough space around the Ni core compared to the TBDAP ligand. The nickel(III) peroxo complexes showed reactivity in the oxidation of aldehydes. In the aldehyde deformylation reaction, the nucleophilic reactivity of the nickel(III) peroxo complexes was highly dependent on the steric properties of the macrocyclic ligands, with a reactivity order of [NiIII(TBDAP)(O2)]+ III(CHDAP)(O2)]+. This result provides fundamental insight into the mechanism of the structure (steric)-reactivity relationship of metal peroxo intermediates. (Figure Presented).

Dual-functional gadolinium-based copper(II) probe for selective magnetic resonance imaging and fluorescence sensing

A unique gadolinium complex, Nap-DO3A-Gd, comprising a naphthylamine luminescent moiety, a di-2-picolylamine (DPA) binding chelator, and a 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DO3A) moiety has been designed and synthesized as a dual-functional probe for selective magnetic resonance imaging and fluorescent sensing of copper(II) in living cells. Nap-DO3A-Gd exhibited a turn-on manner of relaxivity changes and a fluorescent quenching toward Cu2+. Through the introduction of naphthalamide into the Gd3+ contrast agent platform to restrict the coordination ability of the DPA chelator and with Gd3+ coordinating to the DPA moiety to turn away the interferences of other metal cations from Cu 2+ detection, the probe featured selective relaxivity changes toward Cu2+ over other metal ions and brought unique Cu2+- specific luminescent responses. The probe was water-soluble with the luminescent detection limit established at 6 ppb and was successfully used for luminescence imaging detection of copper(II) in living cells. The results demonstrated the efficiency and advantage of our approach in the development of a dual-modality image.

A New Oxygen Containing Pyclen-Type Ligand as a Manganese(II) Binder for MRI and 52Mn PET Applications: Equilibrium, Kinetic, Relaxometric, Structural and Radiochemical Studies

A new pyclen-3,9-diacetate derivative ligand (H23,9-OPC2A) was synthesized possessing an etheric O-atom opposite to the pyridine ring, to improve the dissociation kinetics of its Mn(II) complex (pyclen = 3,6,9,15-tetraazabicyclo(9.3.1)pentadeca

A selective and sensitive near-infrared fluorescent probe for real-time detection of Cu(i)

The disruption of copper homeostasis (Cu+/Cu2+) may cause neurodegenerative disorders. Thus, the need for understanding the role of Cu+ in physiological and pathological processes prompted the development of improved methods of Cu+ analysis. Herein, a new near-infrared (NIR) fluorescent turn-on probe (NPCu) for the detection of Cu+ was developed based on a Cu+-mediated benzylic ether bond cleavage mechanism. The probe showed high selectivity and sensitivity toward Cu+, and was successfully applied for bioimaging of Cu+ in living cells. This journal is

Fast and Efficient Nickel(II)-catalysed Transfer Hydrogenation of Quinolines with Ammonia Borane

Herein we report the first Ni(II)-catalysed transfer hydrogenation of quinolines using ammonia borane (AB) as hydrogen (H2) source. An in situ generated Ni(II)-bis(pyrazolyl)pyridine pre-catalyst could hydrogenate quinoline and its derivatives in excellent yields of up to 90% at 25 °C in 30 minutes. Spectroscopic studies revealed that a Ni(II)-hydride is responsible for the transfer hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline via a 1,4-dihydroquinoline intermediate. (Figure presented.).

Novel cuprous ion near-infrared probe, and preparation method and application thereof

The invention discloses a near-infrared fluorescent probe which is provided with a novel receptor structure (N3O), and has a specific response to cuprous ions in an aqueous solution system, and the problems of poor selectivity and low sensitivity of the c