620-87-1

Basic information

• Product Name: 2-(P-NITROBENZYL)PYRIDINE
• Synonyms: 2-(4-Nitrobenzyl)pyridine;2-[(4-nitrophenyl)methyl]-pyridin;Pyridine, 2-((4-nitrophenyl)methyl)-;Pyridine, 2-(4-nitrobenzyl)-;Pyridine, 2-(p-nitrobenzyl)-;TIMTEC-BB SBB008013;2-(P-NITROBENZYL)PYRIDINE;2-[(4-Nitrophenyl)methyl]pyridine
• CAS NO: 620-87-1
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Mol File: 620-87-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 78-80°C
• Boiling Point: 363.2ºC at 760 mmHg
• Flash Point: 173.5ºC
• Appearance: /
• Density: 1.231g/cm3
• Vapor Pressure: 3.83E-05mmHg at 25°C
• Refractive Index: 1.608
• PKA: 4.83±0.10(Predicted)
• CAS DataBase Reference: 2-(P-NITROBENZYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(P-NITROBENZYL)PYRIDINE(620-87-1)
• EPA Substance Registry System: 2-(P-NITROBENZYL)PYRIDINE(620-87-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 620-87-1(Hazardous Substances Data)

Usage

General Description

2-(p-nitrobenzyl)pyridine is a chemical compound that consists of a pyridine ring with a p-nitrobenzyl group attached at the 2 position. It is used in the synthesis of organic compounds, particularly in the field of pharmaceuticals and agrochemicals. The p-nitrobenzyl group is often used as a protecting group in organic synthesis, and the presence of the pyridine ring imparts specific reactivity and properties to the compound. This chemical is commonly used as a precursor in the production of various drugs, and its reactivity and versatility make it a valuable building block in organic chemistry research and industrial applications.

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 
• 4377-33-7 2-chloromethylpyridine 
• 98-95-3 nitrobenzene 
• 20531-86-6 2-benzylpyridine-N-oxide 
• 1201003-33-9 6-(4-nitrophenyl)hex-5-ynal oxime 

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 
• 58498-11-6 2-(4'-hydroxybenzyl)pyridine 
• 68902-03-4 (2,4-dinitrophenyl)(pyridin-2-yl)methanone 
• 71721-58-9 2-(2,4-dinitro-benzyl)-1-methyl-pyridinium; iodide 
• 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 

Relevant articles and documents

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.

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).