2-Nitrophenol

Base Information

• Chemical Name: 2-Nitrophenol
• CAS No.: 88-75-5
• Deprecated CAS: 1773488-60-0
• Molecular Formula: C6H5NO3
• Molecular Weight: 139.111
• Hs Code.: 2908.90 Oral rat LD50: 334 mg/kg
• European Community (EC) Number: 201-857-5
• ICSC Number: 0523
• NSC Number: 1552
• UN Number: 1663
• UNII: BD148E95KD
• DSSTox Substance ID: DTXSID1021790
• Nikkaji Number: J355G
• Wikipedia: Nitrophenol
• Wikidata: Q18907378
• Metabolomics Workbench ID: 50436
• ChEMBL ID: CHEMBL14205
• Mol file: 88-75-5.mol

Synonyms:2-nitrophenol;2-nitrophenol, ammonium salt;2-nitrophenol, sodium salt;ortho-nitrophenol

Chemical Property of 2-Nitrophenol

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 0.0987mmHg at 25°C
• Melting Point: 43-47 °C
• Boiling Point: 215.8 °C at 760 mmHg
• PKA: 7.14±0.14(Predicted)
• Flash Point: 97.1 °C
• PSA: 66.05000
• Density: 1.395 g/cm³
• LogP: 1.82360
• Water Solubility.: 2 g/L (25℃)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 139.026943022
• Heavy Atom Count: 10
• Complexity: 131
• Transport DOT Label: Poison

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn, T, F
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R33:
• Safety Statements: S36/37:; S45:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin. Ingestion could cause effects on the blood. This may result in the formation of methaemoglobin.

Technology Process of 2-Nitrophenol

There total 331 articles about 2-Nitrophenol 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: 45.0%

nitrobenzene (98-95-3,26969-40-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

With Cumene hydroperoxide; potassium tert-butylate; ammonia; In tetrahydrofuran; for 0.25h;

DOI:10.1021/jo00304a001

Reference yield: 40.0%

phenol (108-95-2,27073-41-2) → 2,4-Dinitrophenol (51-28-5) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + p-benzoquinone (106-51-4) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

With trinitratooxovanadium(V); In dichloromethane; for 0.00833333h; Further byproducts given; Ambient temperature;

DOI:10.1039/a801771i

Reference yield: 17.0%

benzene oxide (1488-25-1) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

With Nitrogen dioxide; at 25 - 30 ℃; for 3h; in the dark;

DOI:10.1248/cpb.30.4566

upstream raw materials:

piperidine

2-Nitroanisole

pyridine

tetranitromethane

Downstream raw materials:

2-(2-hydroxyethoxy)nitrobenzene

2-Nitro-4-piperidinomethyl-phenol

4-(2-(2-nitrophenoxy)ethyl)morpholine

4-(2-nitro-phenoxy)-pyridine

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.