108338-19-8

Basic information

• Product Name: 4-Nitropicolinaldehyde
• Synonyms: 4-Nitropicolinaldehyde;4-Nitro-2-pyridinecarbaldehyde;4-Nitro-2-pyridinecarboxaldehyde
• CAS NO: 108338-19-8
• Molecular Formula: C₆H₄N₂O₃
• Molecular Weight: 152.109
• Mol File: 108338-19-8.mol

Chemical Properties

• Boiling Point: 275.3±25.0℃ (760 Torr)
• Flash Point: 120.3±23.2℃
• Appearance: /
• Density: 1.432±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00515mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.21±0.10(Predicted)
• CAS DataBase Reference: 4-Nitropicolinaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitropicolinaldehyde(108338-19-8)
• EPA Substance Registry System: 4-Nitropicolinaldehyde(108338-19-8)

Safety Data

• Hazardous Substances Data: 108338-19-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Nitropicolinaldehyde is used as a key intermediate in the synthesis of various chemical compounds, particularly in the pharmaceutical and agrochemical industries. Its reactivity and functional groups make it a valuable building block for the development of new molecules with potential applications in drug discovery and crop protection.
Used in Research and Development:
4-Nitropicolinaldehyde is employed as a research compound in academic and industrial laboratories, where it is used to study its chemical properties, reactivity, and potential applications in various fields. Researchers utilize this compound to explore new reaction pathways, develop novel synthetic methods, and investigate its interactions with other molecules.
Used in Material Science:
In the field of material science, 4-Nitropicolinaldehyde is used as a precursor for the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics. Its incorporation into polymers, composites, or other materials can lead to the creation of advanced materials with potential applications in electronics, sensors, or energy storage devices.
Used in Analytical Chemistry:
4-Nitropicolinaldehyde is utilized as a reagent or analytical standard in various analytical techniques, such as chromatography, spectroscopy, or electrochemistry. Its unique chemical properties make it suitable for the detection, quantification, or identification of specific compounds in complex mixtures, contributing to the advancement of analytical methods and techniques.

InChI:InChI=1/C6H4N2O3/c9-4-5-3-6(8(10)11)1-2-7-5/h1-4H

Upstream product

• 98197-88-7 4-nitro-2-(hydroxymethyl)pyridine 
• 36625-64-6 2-hydroxymethyl-4-nitropyridine 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 131747-33-6 2-acetoxymethyl-4-nitropyridine 
• 931-19-1 2-methylpyridine N-oxide 
• 131747-32-5 2-acetoxymethyl-4-nitropyridine 
• 109-06-8 α-picoline 

Downstream Products

• 108337-77-5 2-(N-Benzyl-N-methylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(4-nitro-2-pyridyl)-3,5-pyridinedicarboxylate 
• 131747-63-2 4-bromo-2-pyridinecarboxaldehyde 

Relevant articles and documents

Discovery and crystallography of bicyclic arylaminoazines as potent inhibitors of HIV-1 reverse transcriptase

Non-nucleoside inhibitors of HIV-1 reverse transcriptase (HIV-RT) are reported that incorporate a 7-indolizinylamino or 2-naphthylamino substituent on a pyrimidine or 1,3,5-triazine core. The most potent compounds show below 10 nanomolar activity towards wild-type HIV-1 and variants bearing Tyr181Cys and Lys103Asn/Tyr181Cys resistance mutations. The compounds also feature good aqueous solubility. Crystal structures for two complexes enhance the analysis of the structure-activity data.

Tuning of the properties of transition-metal bispidine complexes by variation of the basicity of the aromatic donor groups

Bispidines (3,7-diazabicyclo[3.3.1]nonanes) as very rigid and highly preorganized ligands find broad application in the field of coordination chemistry, and the redox potentials of their transition-metal complexes are of importance in oxidation reactions by high-valent iron complexes, aziridination catalyzed by copper complexes, and imaging by 64Cu positron emission tomography tracers. Here, we show that the redox potentials and stability constants of the copper(II) complexes of 15 tetradentate bispidines can be varied by substitution of the pyridine rings (variation of the redox potential over ca. 450 mV and of the complex stability over approximately 10 log units). It is also shown that these variations are predictable by the pKa values of the pyridine groups as well as by the Hammett parameters of the substituents, and the density functional theory based energy decomposition analysis also allows one to accurately predict the redox potentials and concomitant complex stability. It is shown that the main contribution emerges from the electrostatic interaction energy, and the partial charges of the pyridine donor groups therefore also correlate with the redox potentials.

A convenient synthetic route to a useful synthon: 4-bromo-2-pyridinecarboxaldehyde

We have developed a novel four-step method to synthesise 4-bromo-2-pyridinecarboxaldehyde, from 2-picoline-N-oxide via 4-nitro-2-pyridinecarboxaldehyde, under mild reaction conditions.

C-H bond oxidation catalyzed by an imine-based iron complex: A mechanistic insight

A family of imine-based nonheme iron(II) complexes (LX)2Fe(OTf)2 has been prepared, characterized, and employed as C-H oxidation catalysts. Ligands LX (X = 1, 2, 3, and 4) stand for tridentate imine ligands resulting from spontaneous condensation of 2-pycolyl-amine and 4-substituted-2-picolyl aldehydes. Fast and quantitative formation of the complex occurs just upon mixing aldehyde, amine, and Fe(OTf)2 in a 2:2:1 ratio in acetonitrile solution. The solid-state structures of (L1)2Fe(OTf)(ClO4) and (L3)2Fe(OTf)2 are reported, showing a low-spin octahedral iron center, with the ligands arranged in a meridional fashion. 1H NMR analyses indicate that the solid-state structure and spin state is retained in solution. These analyses also show the presence of an amine-imine tautomeric equilibrium. (LX)2Fe(OTf)2 efficiently catalyze the oxidation of alkyl C-H bonds employing H2O2 as a terminal oxidant. Manipulation of the electronic properties of the imine ligand has only a minor impact on efficiency and selectivity of the oxidative process. A mechanistic study is presented, providing evidence that C-H oxidations are metal-based. Reactions occur with stereoretention at the hydroxylated carbon and selectively at tertiary over secondary C-H bonds. Isotopic labeling analyses show that H2O2 is the dominant origin of the oxygen atoms inserted in the oxygenated product. Experimental evidence is provided that reactions involve initial oxidation of the complexes to the ferric state, and it is proposed that a ligand arm dissociates to enable hydrogen peroxide binding and activation. Selectivity patterns and isotopic labeling studies strongly suggest that activation of hydrogen peroxide occurs by heterolytic O-O cleavage, without the assistance of a cis-binding water or alkyl carboxylic acid. The sum of these observations provides sound evidence that controlled activation of H2O2 at (LX)2Fe(OTf)2 differs from that occurring in biomimetic iron catalysts described to date.

PHTHALAZINONE DERIVATIVES

A compound of the formula (I): wherein: A and B together represent an optionally substituted, fused aromatic ring; D is selected from: (i) ?where Y1 is selected from CH and N, Y2 is selected from CH and N, Y3 is selected f

Synthesis and Properties of 3-, 4-, and 5-Nitro-2-pyridinecarbaldehyde 2-pyridylhydrazones and Characterization of Their Metal Complexes

Three hydrazones, 3-, 4-, and 5-nitro-2-pyridinecarbaldehyde 2-pyridylhydrazones, were synthesized.Their properties and reactivities with metal ions and the extraction and characteristics of the resultant complexes have been investigated and compared with one another.As a result, useful information on the molecular design of highly sensitive hydrazone reagents has been obtained.