3-Hydroxy-2-nitropyridine

Base Information

• Chemical Name: 3-Hydroxy-2-nitropyridine
• CAS No.: 15128-82-2
• Molecular Formula: C5H4N2O3
• Molecular Weight: 140.098
• Hs Code.: 29333990
• European Community (EC) Number: 239-191-2,604-788-2
• NSC Number: 97501
• UNII: UU357X85YB
• DSSTox Substance ID: DTXSID6022264
• Nikkaji Number: J3.776A
• Wikidata: Q27291274
• Mol file: 15128-82-2.mol

Synonyms:3-hydroxy-2-nitropyridine

Chemical Property of 3-Hydroxy-2-nitropyridine

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 2.02E-06mmHg at 25°C
• Melting Point: 69-71 °C(lit.)
• Refractive Index: 1.623
• Boiling Point: 383.2 °C at 760 mmHg
• PKA: 0.31±0.22(Predicted)
• Flash Point: 185.6 °C
• PSA: 78.94000
• Density: 1.507 g/cm³
• LogP: 1.21860
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 140.02219199
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

98%, ^*data from raw suppliers

3-Hydroxy-2-nitropyridine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)[N+](=O)[O-])O
• General Description: 3-Hydroxy-2-nitropyridine, also known as 2-nitro-3-hydroxypyridine or 2-nitropyridin-3-ol, is a key precursor in the synthesis of pyridoxazinone derivatives with notable antimicrobial properties. Derived from this compound, the pyridoxazinone series demonstrated significant antibacterial activity, particularly against Gram-negative bacteria such as *Enterococcus faecalis* and *Acinetobacter baumannii*, with MIC values as low as 7.8 μg/mL. Additionally, certain derivatives exhibited potent antifungal effects against *Candida* species. The pyridine ring in these analogs was identified as critical for enhancing antimicrobial efficacy, while the compounds maintained low toxicity and favorable drug-like properties. These findings highlight its potential as a scaffold for developing novel antimicrobial agents.

Technology Process of 3-Hydroxy-2-nitropyridine

There total 5 articles about 3-Hydroxy-2-nitropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

3-ethoxy-2-nitropyridine (74037-50-6) → 3-hydroxy-2-nitropyridine (15128-82-2)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; water; at 90 ℃; for 12h;

DOI:10.1021/ol047688v

Reference yield: 60.0%

3-HYDROXYPYRIDINE (109-00-2) → 3-hydroxy-2-nitropyridine (15128-82-2)

Guidance literature:

With aluminium trinitrate; In acetonitrile; at 50 ℃; regioselective reaction;

DOI:10.1021/acs.orglett.8b04141

Reference yield:

3-hydroxypyridine nitrate → 3-hydroxy-2-nitropyridine (15128-82-2)

Guidance literature:

With sulfuric acid; at 50 ℃;

upstream raw materials:

3-HYDROXYPYRIDINE

3-ethoxy-2-nitropyridine

Downstream raw materials:

benzoic acid-(2-nitro-[3]pyridyl ester)

3-methoxy-2-nitropyridine

2-bromo-pyridin-3-ol

2-amino-3-hydroxypyridine

Refernces

Synthesis and antimicrobial activity of some benzoxazinoids derivatives of 2-nitrophenol and 3-hydroxy-2-nitropyridine

10.1080/00397911.2018.1554146

The research aimed to develop new antimicrobial agents by synthesizing and testing benzoxazinoids (BXs) analogs derived from 2-nitrophenol (benzoxazinone series) and 3-hydroxy-2-nitropyridine (pyridoxazinone series). The study employed nucleophilic substitution and reductive cyclization to functionalize these compounds. The synthesized analogs were then tested for their antimicrobial activity against various bacterial and fungal strains. The results showed that the pyridoxazinone series exhibited significant antibacterial activity, particularly against Enterococcus faecalis and Acinetobacter baumannii, with minimum inhibitory concentrations (MICs) ranging from 7.8 to 125 μg/mL. The benzoxazinone series also demonstrated antibacterial activity, though to a lesser extent. In terms of antifungal activity, compound 2e from the pyridoxazinone series was particularly effective against Candida species, with an MIC of 62.5 μg/mL. The study concluded that these BXs analogs have potential as new antimicrobial agents due to their efficacy and low toxicity, as all analogs complied with Lipinski’s rules and were predicted to have low toxicity. The presence of a pyridine ring in the pyridoxazinone series was identified as a key factor enhancing antibacterial activity against Gram-negative bacteria.