1151-97-9

Usage

Uses

Used in Organic Synthesis:
2-(2,4-DINITROBENZYL)PYRIDINE is used as a building block in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Intermediates:
In the pharmaceutical industry, 2-(2,4-DINITROBENZYL)PYRIDINE serves as an intermediate in the development of new drugs. Its chemical properties can be exploited to create novel drug candidates with potential therapeutic applications.
Chemical Properties:
The compound is known for its white to yellow to green powder or crystalline form, which is indicative of its solid-state structure. The presence of the 2,4-dinitrobenzyl group on the pyridine ring endows the molecule with specific reactivity and stability characteristics, making it suitable for use in various chemical and pharmaceutical applications.

Preparation

Synthesis of 2-(2,4-Dinitrobenzyl)pyridineA solution of sulfuric acid (15 mL) is placed in an ice bath along with a magnetic stirrer.Benzylpyridine (2.4 mL) is added dropwise, maintaining a temperature below 10°C. This process is then repeated for fuming nitric acid (3.0 mL), once again maintaining the temperature. After addition mixture is allowed to stand at room temperature for 30minutes. Once completed reaction mixture is heated in an 80°C water bath for 20 minutes. Mixture is then poured into a conical flask containing crushed ice (50 cm3) which is stirred in an ice bath. Using a separating funnel aqueous ammonia is added (50 – 100 mL) until the pH rises to ~9 – 10 and filter using a Buchner funnel. Ethyl acetate (40mL) & sodium hydroxide (40mL) is added to the solid and stirred using a magnetic stirrer until dissolved.Dry the organic layer using magnesium sulfate as the drying agent which is then followed by a rotary evaporator (40°C, vacuum). Product is then washed using cold methylated spirit and left to recrystalise.

InChI:InChI=1/C12H9N3O4/c16-14(17)11-5-4-9(12(8-11)15(18)19)7-10-3-1-2-6-13-10/h1-6,8H,7H2

Upstream product

• 584-48-5 2,4-dinitrobromobenzene 
• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 109-06-8 α-picoline 
• 4377-33-7 2-chloromethylpyridine 
• 99-65-0 meta-dinitrobenzene 
• 101-82-6 2-Benzylpyridine 
• 7664-93-9 sulfuric acid 
• 70938-75-9 2-(2,4-dinitro-benzylidene)-1,2-dihydro-pyridine 
• 70938-75-9 2-[1-(2,4-Dinitro-phenyl)-meth-(E)-ylidene]-1,2-dihydro-pyridine 
• 620-87-1 2-(4-nitrobenzyl)pyridine 

Downstream Products

• 71721-58-9 2-(2,4-dinitro-benzyl)-1-methyl-pyridinium; iodide 
• 63233-62-5 4-[2]pyridylmethyl-m-phenylenediamine 
• 70938-75-9 2-(2,4-dinitro-benzylidene)-1,2-dihydro-pyridine 
• 68902-03-4 (2,4-dinitrophenyl)(pyridin-2-yl)methanone 
• 50678-83-6 (2-nitrophenyl)(pyridin-2-yl)methanone 
• 13347-69-8 2-(2-nitrobenzyl)pyridine 
• 53114-00-4 2-(2-aminobenzyl)pyridine 
• 1222-41-9 6-aci-nitro-2-nitro-5-(2'-pyridylmethylene)-1,3-cyclohexadiene 
• 13347-70-1 2-(4'-Amino-2'-nitrobenzyl)pyridin 
• 1222-41-9 2-[4-Nitro-6-aci-nitro-cyclohexa-2,4-dien-(E)-ylidenemethyl]-pyridine 
• 70938-75-9 2-[1-(2,4-Dinitro-phenyl)-meth-(E)-ylidene]-1,2-dihydro-pyridine 

Relevant academic research and scientific papers

Evidence for two competing mechanisms in regeneration of 2-(2,4-dinitrobenzyl)pyridine from its enamine tautomer

Kinetic effects of pressure on the title reaction were studied. The reaction was insensitive to a change in pressure at 0.1 MPa, however, it was accelerated by an increase in pressure at P > 100 MPa, showing the existence of two reaction routes with and without solvent participation. Viscosity-induced retardations observed in highly viscous media supported intervention of solvent molecules at high pressures.

TAUTOMERISM OF 2-(2,4-DINITROBENZYL)PYRIDINE

The Equilibrium constans for imine-enamine and aci-nitro tautomerism of 2-(2,4-dinitrobenzyl)pyridine have been determined as 7.5E-9 and 3E-14 respectively.

Efficient Selenium-Catalyzed Selective C(sp3)?H Oxidation of Benzylpyridines with Molecular Oxygen

An efficient selenium-catalyzed direct oxidation of benzylpyridines in aqueous DMSO has been successfully developed by using molecular oxygen as the oxidant. A variety of benzoylpyridines with broad functional group tolerance were obtained in modest to excellent yields and with exclusive chemoselectivity. (Figure presented.).

Vicarious nucleophilic substitution of (chloroalkyl)heterocycles with nitroarenes

The vicarious nucleophilic substitution of potassium carbanions of the (chloromethyl)pyridines 1a and 1b, (chloromethyl)benzothiazole 1c, (chloromethyl)thiazole 1d, (chloroethyl)thiazole 1e and (chloroethyl) benzothiazole 1f wit nitroarenes, leading to ni

Proton-Transfer Processes in Well-Defined Media: Experimental Investigation of Photoinduced and Thermal Proton-Transfer Processes in Single Crystals of 2-(2,4-Dinitrobenzyl)pyridine Derivatives

A detailed spectroscopic study of photoinduced and thermally activated proton-transfer processes for a series of different crystals of 2-(2,4-dinitrobenzyl)pyridine derivatives has been performed.The quantitative analysis of ground- and excited-state activation barriers and preexponential factors in deuterated and nondeuterated crystals shows clearly that the observed photochromism is linked to a proton-transfer process.Furthermore, it is clearly seen that the supramolecular environment of the transferred proton participates in the proton-transfer process.These supramolecular effects control the relative rates and efficiencies of the observed proton-transfer processes in both the ground and excited state, yielding, at room temperature, photoproducts having lifetimes ranging between hours and weeks.At least two proton-accepting groups may be active in the abstraction of the proton from its relatively stable benzylic position.Additionally, low-temperature measurements of proton-transfer processes show that tunneling processes prevail at temperatures below 100 K only in the excited state.No evidence for tunneling could be found for ground-state processes.

Long-lived Photoinduced Proton Transfer Processes

Irradiation of the phenanthroline-dinitrobenzyl compound 3 generates, via a photoinduced proton transfer process, a long-lived tautomer having a lifetime about 5*103 times longer than that of the parent compound 1a.