32896-91-6

Basic information

• Product Name: 3-nitro-1-methyl-2(1H)-pyridinone
• Synonyms: 3-nitro-1-methyl-2(1H)-pyridinone;1-Methyl-3-nitropyridin-2(1H)-one
• CAS NO: 32896-91-6
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12344
• Mol File: 32896-91-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 314.1°Cat760mmHg
• Flash Point: 143.8°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.000476mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: 2-8°C
• PKA: -5.28±0.62(Predicted)
• CAS DataBase Reference: 3-nitro-1-methyl-2(1H)-pyridinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitro-1-methyl-2(1H)-pyridinone(32896-91-6)
• EPA Substance Registry System: 3-nitro-1-methyl-2(1H)-pyridinone(32896-91-6)

Safety Data

• Hazardous Substances Data: 32896-91-6(Hazardous Substances Data)

Usage

Description

3-nitro-1-methyl-2(1H)-pyridinone, also known as N-methyl-3-nitro-2-pyridone, is a chemical compound with the molecular formula C6H6N2O3. It is a nitro derivative of pyridinone and is characterized by its pale yellow crystalline powder form. 3-nitro-1-methyl-2(1H)-pyridinone is soluble in organic solvents and stable under normal conditions, making it a versatile intermediate in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
3-nitro-1-methyl-2(1H)-pyridinone is used as an intermediate in the production of antibiotics and other medicinal products. Its unique chemical structure contributes to the development of new pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 3-nitro-1-methyl-2(1H)-pyridinone is utilized as a key component in the formulation of pesticides. Its strong bactericidal and fungicidal properties make it an effective agent for controlling a wide range of plant diseases and pests, thereby enhancing crop protection and yield.
Used in Anti-infective Medications:
3-nitro-1-methyl-2(1H)-pyridinone is employed as an active ingredient in anti-infective medications. Its potent antimicrobial activity aids in the treatment of various bacterial and fungal infections, contributing to the development of effective therapeutic options for patients.

InChI:InChI=1/C6H6N2O3/c1-7-4-2-3-5(6(7)9)8(10)11/h2-4H,1H3

Upstream product

• 6332-56-5 2-hydroxy-3-nitropyridine 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 6332-56-5 3-nitropyridone 

Downstream Products

• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 33631-01-5 3-amino-1-methyl-2(1H)-pyridinone 

Relevant articles and documents

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Palladium-catalyzed directed synthesis ofortho-deuterated phenylacetic acid and analogues

The synthesis of deuterium-labeled organic compounds is of increased interest, especially after the approval of deutetrabenazine by the Food and Drug Administration in 2014. The selective incorporation of deuterium in the place of hydrogen not only represents uniqueness in terms of a novel chemical class, but it also can improve the pharmacokinetic profiles of drug molecules while retaining potency and other parameters; thus, hydrogen-deuterium (H/D) exchange methods have been proven to be powerful additions in different areas of chemical science. In that regard, metal-catalyzed deuterium labelingviaC-H activation mediated by a unique inbuilt directing group (DG) can play a significant role in the synthesis of novel deuterated chemical entities. In this context, herein, we divulge our results relating to Pd(ii)-catalyzed deuterium incorporation (>97%) at the γ C(sp2)-position of pyridone-containing phenylacetic acid derivatives, where 3-amino-1-methyl-1H-pyridin-2-one (AMP) not only acts as an efficientN,O-directing group, but it also constitutes a part of the target molecules of medicinal importance. Our methodology, which has been optimized based on the effects of temperature, catalyst, time, and substrate scope, shows advantages over existing protocols, with non-selectivity or meager deuteration or the use of an expensive metal (catalytic or super stoichiometric) and a deuterated solvent, reported previously for the deuteration of phenylacetic acid and its derivatives. Moreover, towards our aim of synthesizing deuterium-labeled biologically relevant compounds, the gram scale synthesis of a deuterated analogue of biphenyl acetic acid (3), known to have activity against epileptic seizures, has also been successfully accomplished in high yields and with excellent isotope enrichmentviaimplementing this protocol.

Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives possessing a dimethylphosphine oxide moiety were designed, synthesized and evaluated as novel Focal adhesion kinase (FAK) inhibitors. Most compounds potently suppressed the enzymatic activities of FAK, with IC50 values in the 10?8–10?9 M range, and potently inhibited the proliferation of breast (MDA-MB-231) and lung (A549) cancer cell lines. The representative compound 25b exhibited potent enzyme inhibition (IC50 = 5.4 nM) and good selectivity when tested on a panel of 26 kinases. 25b exhibited antiproliferative activity against A549 cells (IC50 = 3.2 μM) and relatively less cytotoxicity to a normal human cell line HK2. Compound 25b also induced apoptosis and suppressed the migration of A549 cells in a concentration-dependent manner. Further profiling of compound 25b revealed it had good metabolic stability in mouse, rat and human liver microsomes in vitro and showed weak inhibitory activity against various subtypes of human cytochrome P450. The docking study of compound 25b was performed to elucidate its possible binding modes and to provide a structural basis for further structure-guided design of FAK inhibitors.