620-87-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(P-NITROBENZYL)PYRIDINE is used as a precursor in the production of various drugs. Its reactivity and versatility make it an essential component in the development of new pharmaceutical compounds, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-(P-NITROBENZYL)PYRIDINE is utilized as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique properties allow for the creation of effective and targeted agrochemical products.
Used in Organic Synthesis Research:
2-(P-NITROBENZYL)PYRIDINE is employed as a valuable building block in organic chemistry research. Its presence in various chemical reactions provides insights into the reactivity and properties of pyridine-based compounds, furthering the understanding of organic synthesis mechanisms and methodologies.
Used as a Protecting Group in Organic Synthesis:
The p-nitrobenzyl group in 2-(P-NITROBENZYL)PYRIDINE is often used as a protecting group in organic synthesis. This allows chemists to temporarily mask functional groups during the synthesis process, preventing unwanted side reactions and facilitating the construction of complex organic molecules.

InChI:InChI=1/C12H10N2O2/c15-14(16)12-6-4-10(5-7-12)9-11-3-1-2-8-13-11/h1-8H,9H2

Upstream product

• 101-82-6 2-Benzylpyridine 
• 20482-09-1 2-(4-nitro-benzyl)-pyridine-1-oxide 
• 87926-08-7 N-methyl-2-(p-nitrobenzyl)pyridinium iodide 
• 7664-93-9 sulfuric acid 
• 1201003-33-9 6-(4-nitrophenyl)hex-5-ynal oxime 
• 20531-86-6 2-benzylpyridine-N-oxide 
• 4377-33-7 2-chloromethylpyridine 
• 98-95-3 nitrobenzene 

Downstream Products

• 87926-08-7 N-methyl-2-(p-nitrobenzyl)pyridinium iodide 
• 58498-12-7 4-(2-Pyridinylmethyl)phenylamine 
• 1151-97-9 2-(2,4-dinitrobenzyl)pyridine 
• 62-23-7 4-nitro-benzoic acid 
• 1304788-89-3 (3R,4S)-4-(4-nitrophenyl)-3-phenyl-4-(pyridin-2-yl)butan-1-ol 
• 1304788-93-9 (3R,4R)-4-(4-nitrophenyl)-3-phenyl-4-(pyridin-2-yl)butan-1-ol 
• 71721-58-9 2-(2,4-dinitro-benzyl)-1-methyl-pyridinium; iodide 
• 68902-03-4 (2,4-dinitrophenyl)(pyridin-2-yl)methanone 
• 58498-11-6 2-(4'-hydroxybenzyl)pyridine 

Relevant academic research and scientific papers

Synthesis of pyridines and pyrazines using an intramolecular hydroamination-based reaction sequence

A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). ρ-Toluenesulfonic acid (2 mol%) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redoxneutral aromatization step to occur.

Affinity of 3-acyl substituted 4-quinolones at the benzodiazepine site of GABAA receptors

The finding that alkyl 1,4-dihydro-4-oxoquinoline-3-carboxylate and N-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxamide derivatives may be high-affinity ligands at the benzodiazepine binding site of the GABAA receptor, prompted a study of 3-acyl-1,4-dihydro-4-oxoquinoline (3-acyl-4-quinolones). In general, the affinity of the 3-acyl derivatives was found to be comparable with the 3-carboxylate and the 3-carboxamide derivatives, and certain substituents (e.g., benzyl) in position 6 were again shown to be important. As it is believed that the benzodiazepine binding site is situated between an α- and a γ-subunit in the GABAA receptor, selected compounds were tested on the α1β2γ2s, α2β2γ2s and α3β2γ2s GABAA receptor subtypes. The 3-acyl-4-quinolones display various degrees of selectivity for α1- versus α2- and α3-containing receptors, and high-affinity ligands essentially selective for α1 over α3 were developed.

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

Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety

In order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC 50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.

Enamine Rearrangement of 2-Benzylpyridinium Salts to 2-Aminobiphenyls

N-Methyl-2-benzylpyridinium iodide (1c) undergoes ring opening and recyclization reactions when heated with methylammonium sulphite to give 2-methylaminobiphenyl (2c), 2-hydroxybiphenyl (3) and 2-benzylpyridine (4).A similar reaction of N-methyl-2-(p-acetylbenzyl)-, N-methyl-2-(p-acetamidobenzyl)-, N-methyl-2-(p-phthalimidobenzyl)-, N-methyl-2-(p-ethylaminobenzyl)-, N-methyl-2-(p-methylethylaminobenzyl)-, and N-methyl-2-butyl-pyridinium iodides (1e, g-k) affords 2-methylamino-4-acetylbiphenyl (2e), 2-methylamino-4-aminobiphenyl (2g = 2h), 2-methylamino-4-ethylaminobiphenyl (2i), 2-methylamino-4-methylethylaminobiphenyl (2j) and N-methyl-2-propylaniline (2k) respectively in good yields.On the other hand, N-methyl-2-(carbamylmethyl)- (1a), N-methyl-2-(cyanomethyl)- (1b) and N-methyl-2-(p-nitrobenzyl)pyridinium iodides (1d) do not undergo such a rearrangement.It has been found that the unquaternized 2-benzylpyridine when heated with methylammonium sulphite undergoes recyclization to 2-methylaminobiphenyl (2k).