112776-84-8

Basic information

• Product Name: Dimethyl 4-iodopyridine-2,6-dicarboxylate
• Synonyms: Dimethyl 4-iodopyridine-2,6-dicarboxylate
• CAS NO: 112776-84-8
• Molecular Formula: C₉H₈INO₄
• Molecular Weight: 321.06859
• Mol File: 112776-84-8.mol

Chemical Properties

• Melting Point: 175 °C(Solv: methanol (67-56-1))
• Boiling Point: 397.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.778±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -2.37±0.10(Predicted)
• CAS DataBase Reference: Dimethyl 4-iodopyridine-2,6-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 4-iodopyridine-2,6-dicarboxylate(112776-84-8)
• EPA Substance Registry System: Dimethyl 4-iodopyridine-2,6-dicarboxylate(112776-84-8)

Safety Data

• Hazardous Substances Data: 112776-84-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Dimethyl 4-iodopyridine-2,6-dicarboxylate is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-nitrogen bonds. Its high reactivity and selectivity make it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Research and Drug Development:
Dimethyl 4-iodopyridine-2,6-dicarboxylate is utilized in pharmaceutical research and drug development as a versatile building block for the preparation of various functionalized molecules. Its unique structure and properties contribute to the discovery and synthesis of new therapeutic agents.

Upstream product

• 67-56-1 methanol 
• 506423-80-9 4-iodo-pyridine-2,6-dicarboxylic acid 
• 5371-70-0 dimethyl 4-chloro-2,6-pyridinedicarboxylate 
• 71022-75-8 4-chloropyridine-2,6-dicarbonyl dichloride 
• 4722-94-5 4-chloro-2,6-pyridinedicarboxylic acid 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 19872-91-4 dimethyl 4-hydroxypyridine-2,6-dicarboxylate 
• 75-36-5 acetyl chloride 
• 138-60-3 chelidamic acid 
• 499-51-4 Chelidamic acid 

Downstream Products

• 112776-85-9 dimethyl 4-[(4-aminophenyl)ethynyl]pyridine-2,6-dicarboxylate 
• 119754-26-6 dimethyl 4-(4-aminophenylethynyl)-2,6-pyridinedicarboxylate 
• 120491-91-0 2,6-bis(hydroxymethyl)-4-iodopyridine 
• 506423-88-7 4-iodopyridine-2,6-dicarbaldehyde 
• 1002724-34-6 dimethyl 4-((4-hexyloxyphenyl)ethynyl)pyridine-2,6-dicarboxylate 
• 741709-66-0 dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate 
• 1009339-36-9 dimethyl 4-(trifluoromethyl)pyridine-2,6-dicarboxylate 
• 1247012-09-4 C₂₃H₂₇NO₆S 
• 1247012-10-7 C₂₄H₂₉NO₈S₂ 
• 1247012-12-9 C₃₁H₄₅N₅O₅S 
• 1247012-13-0 C₄₀H₅₇N₅O₁₁S 
• 210155-50-3 2,6-(2,6-(i)Pr₂-C₆H₃N=CMe)2-4-CF₃-C₅H₂N 
• 1435951-13-5 2,6-bis((2-(4-(2-(allyloxy)ethoxy)phenoxy)ethoxy)methyl)-4-iodopyridine 

Relevant articles and documents

Efficient formation of luminescent lanthanide(III) complexes by solid-phase synthesis and on-resin screening

Time-resolved luminescence measurements of luminescent lanthanide complexes have advantages in biological assays and high-throughput screening, owing to their high sensitivity. In spite of the recent advances in their energy-transfer mechanism and molecular-orbital-based computational molecular design, it is still difficult to estimate the quantum yields of new luminescent lanthanide complexes. Herein, solid-phase libraries of luminescent lanthanide complexes were prepared through amide-condensation and Pd-catalyzed coupling reactions and their luminescent properties were screened with a microplate reader. Good correlation was observed between the time-resolved luminescence intensities of the solid-phase libraries and those of the corresponding complexes that were synthesized by using liquid-phase chemistry. This method enabled the rapid and efficient development of new sensitizers for SmIII, EuIII, and TbIII luminescence. Thus, solid-phase combinatorial synthesis combined with on-resin screening led to the discovery of a wide variety of luminescent sensitizers. La confidential: Solid-phase synthesis by using amide-condensation and Pd-coupling reactions enabled the efficient development of new antenna ligands for SmIII, EuIII, and Tb III atoms for discovering a wide variety of luminescent sensitizers. Copyright

Organoarsenic probes to study proteins by NMR spectroscopy

Arsenical probes enable structural studies of proteins. We report the first organoarsenic probes for nuclear magnetic resonance (NMR) and electron paramagnetic resonance (EPR) spectroscopy to study proteins in solutions. These probes can be attached to ir

Electron transfer pathways in photoexcited lanthanide(iii) complexes of picolinate ligands

A series of luminescent lanthanide(iii) complexes consisting of 1,4,7-triazacyclononane frameworks and three secondary amide-linked carbostyril antennae were synthesised. The metal binding sites were augmented with two pyridylcarboxylate donors yielding octadentate ligands. The antennae carried methyl, methoxymethyl or trifluoromethyl substituents in their 4-positions, allowing for a range of excited state energies and antenna electronic properties. The1H NMR spectra of the Eu(iii) complexes were found to be analogous to each other. Similar results were obtained in the solid-state by single-crystal X-ray crystallography, which showed the structures to have nine-coordinate metal ions with heavily distorted tricapped trigonal prismatic geometries. Steady-state and time-resolved luminescence spectroscopy showed that the antennae could sensitize both Tb(iii) and Eu(iii), however, quantum yields were lower than in other octadentate complexes lacking pyridylcarboxylate. Complexes with more electron-poor pyridines were less emissive even when equipped with the same antenna. The oxidation and reduction potentials of the antennae and the pyridinecarboxylates, respectively, were determined by cyclic voltammetry. The obtained values were consistent with electron transfer from the excited antenna to the pyridine providing a previously unexplored quenching pathway that could efficiently compete with energy transfer to the lanthanide. These results show the crucial impact that photophysically innocent ligand binding sites can have on lanthanide luminescence.

Luminescent Carbazole-Based EuIII and YbIII Complexes with a High Two-Photon Absorption Cross-Section Enable Viscosity Sensing in the Visible and near IR with One- And Two-Photon Excitation

The newly synthesized EuIII and YbIII complexes with the new carbazole-based ligands CPAD2- and CPAP4- display the characteristic long-lived metal-centered emission upon one- and two-photon excitation. The EuIII complexes show the expected narrow emission bands in the red region, with emission lifetimes between 0.382 and 1.464 ms and quantum yields between 2.7% and 35.8%, while the YbIII complexes show the expected emission in the NIR region, with emission lifetimes between 0.52 and 37.86 μs and quantum yields between 0.028% and 1.12%. Two-photon absorption cross sections (σ2PA) as high as 857 GM were measured for the two ligands. The complexes showed a strong dependence of the one- and two-photon sensitized emission intensity on solvent viscosity in the range of 0.5-200 cP in the visible and NIR region.

Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups

The number of substituted pyridine pyridinophanes found in the literature is limited due to challenges associated with 12-membered macrocycle and modified pyridine synthesis. Most notably, the electrophilic character at the 4-position of pyridine in pyridinophanes presents a unique challenge for introducing electrophilic chemical groups. Likewise, of the few reported, most substituted pyridine pyridinophanes in the literature are limited to electron-donating functionalities. Herein, new synthetic strategies for four new macrocycles bearing the electron-withdrawing groups CN, Cl, NO2, and CF3 are introduced. Potentiometric titrations were used to determine the protonation constants of the new pyridinophanes. Further, the influence of such modifications on the chemical behavior is predicted by comparing the potentiometric results to previously reported systems. X-ray diffraction analysis of the 4-Cl substituted species and its Cu(II) complex are also described to demonstrate the metal binding nature of these ligands. DFT analysis is used to support the experimental findings through energy calculations and ESP maps. These new molecules serve as a foundation to access a range of new pyridinophane small molecules and applications in future work.

SUBSTITUTED PYRIDINE COMPOUNDS AS PESTICIDES

The present invention relates to novel substituted pyridine compounds of the formula (I) in which R1, R2, R3, R4, R5, R6, V1, V2 and Q1 have the definitions

WATER-SOLUBLE TRIAZAPYRIDINOPHANE-BASED COMPLEXING AGENTS AND CORRESPONDING FLUORESCENT LANTHANIDE COMPLEXES

The invention relates to complexing agents of formula (I) in which A1, A2, A3 and R1 are as defined in the description. The invention also relates to lanthanide complexes obtained from said complexing agents. The invention can be used for marking biological molecules.

LANTHANIDE COMPLEXES FOR CRYSTALLISING BIOLOGICAL MACROMOLECULES AND DETERMINING THE CRYSTALLOGRAPHIC STRUCTURE THEREOF

The invention relates to cationic complexes made up of a lanthanide ion Ln3+ and a ligand of formula (I) : with X, Y and R1 as defined in claim 1, and to the salts thereof with an anion, the solvates and hydrates thereof; with the exception of cationic complexes made up of a lanthanide ion Ln3+ and a ligand of one of formulae (I.1) or (I.4) as defined in claim 1, and the salts, solvates and hydrates thereof. The invention also relates to the use of such a complex or of a cationic complex made up of a lanthanide ion Ln3+ and a ligand of formula (I.1) or (I.4) as defined in claim 1, or of one of the salts thereof with an anion, the solvates or hydrates thereof, as an aid to the crystallisation of a biological macromolecule, as well as to crystallisation methods and methods for analysing or determining the structure of a biological macromolecule.

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.

Synthesis and Hydrolysis of 4-Chloro-PyMTA and 4-Iodo-PyMTA Esters and Their Oxidative Degradation with Cu(I/II) and Oxygen

We disclose the syntheses of ethyl and tert-butyl esters of 4-chloro-PyMTA and 4-iodo-PyMTA from the commercially available chelidamic acid monohydrate in 39-67% overall yield. Additionally, ester hydrolyses with aqueous NaOH (ethyl esters) or trifluoroacetic acid (tert-butyl esters) are reported. The resulting materials contain 4-halo-PyMTA in mixture with partially deprotonated or partially protonated 4-halo-PyMTA. The ligand content expressed as the content of the common structural motifs of the present species, namely [PyMTA - 4 H+4- (basic hydrolysis) and PyMTA (acidic hydrolysis), was determined to be 90-94 wt % by1H NMR spectroscopy using maleic acid as an internal standard. The tert-butyl esters were easily hydrolyzed with aqueous alkali hydroxide, with a decreasing rate in the series NaOH, KOH, LiOH. This finding indicates a Lewis acid assisted ester cleavage with the Na+ ion fitting best to the multidentate ligand. Unexpectedly, PyMTA esters are incompatible with Cu(I/II) salts in the presence of oxygen. Under these conditions, one of the two aminomethyl groups is converted into a formyl group. This reaction not only limits the application of Cu(I/II)-catalyzed reactions but also necessitates trapping of any copper ions (e.g., with a metal ion scavenger) before the material is exposed to oxygen.