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4-Nitrophenol

Base Information Edit
  • Chemical Name:4-Nitrophenol
  • CAS No.:100-02-7
  • Deprecated CAS:856824-67-4,856824-71-0,856824-71-0
  • Molecular Formula:C6H5NO3
  • Molecular Weight:139.111
  • Hs Code.:2908.90 Oral rat LD50: 202 mg/kg
  • European Community (EC) Number:202-811-7
  • ICSC Number:0066
  • NSC Number:1317
  • UN Number:1663
  • UNII:Y92ZL45L4R
  • DSSTox Substance ID:DTXSID0021834
  • Nikkaji Number:J351.565F
  • Wikipedia:4-nitrophenol
  • Wikidata:Q656269
  • Metabolomics Workbench ID:37674
  • ChEMBL ID:CHEMBL14130
  • Mol file:100-02-7.mol
4-Nitrophenol

Synonyms:4-nitrophenol;4-nitrophenol, (18)O-labeled cpd;4-nitrophenol, 1-(13)C-labeled cpd;4-nitrophenol, 14C-labeled cpd;4-nitrophenol, 2,6-(13)C2-labeled cpd;4-nitrophenol, 2,6-(14)C2-labeled cpd;4-nitrophenol, 2-(14)C-labeled cpd;4-nitrophenol, aluminum salt;4-nitrophenol, ammonium salt;4-nitrophenol, cesium salt;4-nitrophenol, copper(1+) salt;4-nitrophenol, ion(1-);4-nitrophenol, ion(1-) hydride;4-nitrophenol, iron(3+) salt;4-nitrophenol, lithium salt;4-nitrophenol, manganese (2+) salt;4-nitrophenol, manganese salt;4-nitrophenol, potassium salt;4-nitrophenol, silver(2+) salt;4-nitrophenol, sodium salt;4-nitrophenol, sodium salt, (2:1), dihydrate;4-nitrophenol, tin (2+) salt;4-nitrophenol, tin (4+) salt;4-nitrophenol, zinc salt;p-nitrophenol

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Chemical Property of 4-Nitrophenol Edit
Chemical Property:
  • Appearance/Colour:Yellow to brown crystals 
  • Vapor Pressure:0.00243mmHg at 25°C 
  • Melting Point:112-114 °C 
  • Refractive Index:1.5723 (estimate) 
  • Boiling Point:279 °C at 760 mmHg 
  • PKA:7.15(at 25℃) 
  • Flash Point:141.9 °C 
  • PSA:66.05000 
  • Density:1.395 g/cm3 
  • LogP:1.82360 
  • Storage Temp.:Store in dark! 
  • Solubility.:ethanol: soluble95%, clear, dark yellow (100 mg/mL) 
  • Water Solubility.:1.6 g/100 mL (25℃) 
  • XLogP3:1.9
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:139.026943022
  • Heavy Atom Count:10
  • Complexity:123
  • Transport DOT Label:Poison
Purity/Quality:
Safty Information:
  • Pictogram(s): HarmfulXn,ToxicT,Flammable
  • Hazard Codes: Xn:Harmful;
     
  • Statements: R20/21/22:; R33:; 
  • Safety Statements: S28A:; 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Nitrophenols
  • Canonical SMILES:C1=CC(=CC=C1[N+](=O)[O-])O
  • Recent ClinicalTrials:Effect of Preoperative Oral Carbohydrates on Quality of Recovery in Laparoscopic Colorectal Surgery Patients
  • Inhalation Risk:Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
  • Effects of Short Term Exposure:The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
  • Effects of Long Term Exposure:Repeated or prolonged contact may cause skin sensitization.
  • General Description 4-Nitrophenol (4-NP) is a nitro-substituted phenolic compound that serves as a substrate in catalytic reduction reactions, such as its conversion to 4-aminophenol (4-AP) by metal nanoparticles (e.g., Au, Ag, Pt, Pd) in the presence of sodium borohydride. It is also utilized as a reagent in organic synthesis, including the preparation of active esters via palladium-catalyzed alkoxycarbonylation of aryl bromides, and as a catalyst in retro-ene fragmentation reactions of allylic dithiolcarbonates. Additionally, 4-NP is employed in biochemical and biomedical research, such as in the synthesis of glycosyl conjugates for antiproliferative studies and as a component in hydrogel fabrication for cell culture applications. Its versatility stems from its reactivity and role as an intermediate in various chemical and catalytic processes.
Technology Process of 4-Nitrophenol

There total 2476 articles about 4-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:
Guidance literature:
With triethylamine; In dimethyl sulfoxide; benzene; at 25 ℃; Equilibrium constant; ionization in solvent mixtures with different ratio;
DOI:10.1021/j100463a022
Refernces Edit

Green synthesis of gold, silver, platinum, and palladium nanoparticles reduced and stabilized by sodium rhodizonate and their catalytic reduction of 4-nitrophenol and methyl orange

10.1039/c8nj01223g

The research focuses on the green synthesis of gold (Au), silver (Ag), platinum (Pt), and palladium (Pd) nanoparticles using sodium rhodizonate as a bifunctional reducing and stabilizing agent. The study involves the preparation of these nanoparticles in water through a single-step process and evaluates their catalytic efficiency in reducing 4-nitrophenol (4-NP) to 4-aminophenol (4-AP) using sodium borohydride (NaBH4) and in the dual-catalytic oxidation of formic acid followed by the reduction of methyl orange (MO). The synthesized nanoparticles were characterized using UV-Vis spectroscopy, transmission electron microscopy (TEM), energy-dispersive X-ray (EDX) spectroscopy, and zeta potential measurements to determine their size, morphology, crystallinity, elemental composition, and surface charge. The catalytic activities of the nanoparticles were assessed through UV-Vis spectrophotometer monitoring of the absorbance changes at specific wavelengths, corresponding to the reactants and products in the reduction reactions.

Cationic hybrid hydrogels from amino-acid-based poly(ester amide): Fabrication, characterization, and biological properties

10.1002/adfm.201103147

The research focuses on the development of a new family of cationic charged biocompatible hybrid hydrogels, based on arginine unsaturated poly(ester amide) (Arg-UPEA) and Pluronic diacrylate (Pluronic-DA), which were fabricated through UV photocrosslinking in an aqueous medium. The purpose of this study was to improve the cellular interactions of synthetic hydrogels for potential biomedical applications by introducing cationic Arg-UPEA, which possesses biocompatibility and cationic properties. The conclusions drawn from the research indicate that the incorporation of Arg-UPEA into Pluronic-DA hydrogels significantly enhanced cell attachment, proliferation, and viability of both Detroit 539 human fibroblasts and bovine aortic endothelial cells. The chemicals used in the process include Pluronic F127, acryloyl chloride, triethylamine, Irgacure 2959 (as a photoinitiator), L-arginine, p-toluenesulfonic acid monohydrate, fumaryl chloride, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and p-nitrophenol, among others. These chemicals were utilized in the synthesis of the hydrogel precursors and for the characterization of their physicochemical properties.

Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide

10.1016/S0014-827X(01)01074-6

The research aimed to synthesize and test the biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide (4-HPR), a synthetic derivative of retinoic acid, on various tumor cell lines. The purpose was to investigate the potential antiproliferative effects and reduced toxicity of these conjugates compared to the parent compound, 4-HPR. The study focused on glucosyl, galactosyl, and mannosyl conjugates, which were synthesized through a five-step process involving the use of peracetylated monosaccharides, bismuth bromide as a catalyst, p-nitrophenol, Pearlman’s catalyst for nitro group reduction, and EDC/DMAP for coupling with RA. The synthesized compounds were then tested for their antiproliferative potential in vitro using four human cancer cell lines and their toxicity on normal cells. The results showed that all three conjugates were active on promyelocytic leukemia cell lines HL60 but were less potent than 4-HPR. Notably, the mannosyl analog (5c) demonstrated significantly lower toxicity than 4-HPR, with a selectivity index close to 15 on HL60 cells, indicating its potential as a less toxic and effective antiproliferative agent.

Retro-ene type fragmentation of allylic dithiolcarbonates

10.1016/0040-4039(96)00314-0

The research investigates the retro-ene type fragmentation of allylic dithiolcarbonates. The study found that the formation of 2-alkenyl alkyl sulfides from S-(2-alkenyl) S-alkyl dithiocarbonates, with the extrusion of COS, is effectively catalyzed by Lewis acids. Phenolic compounds, such as p-nitrophenol, also showed catalytic activity, promoting the reaction through an SNi'-type mechanism involving the attack of the alkylthio group on the β-carbon atom of the allylic system, with simultaneous double bond shift and COS elimination. The use of aluminum catalysts, like AlCl3 and Me2AlCl, resulted in significant rate enhancements, with the reaction proceeding smoothly at room temperature to yield sulfides in high quantities. The research also involved molecular orbital calculations on a model reaction pathway of S-allyl S-methyl dithiocarbonate (2A) to establish the reaction mechanism. The calculations indicated that the reaction barrier was lowered in the presence of AlCl3 and that the nature of the concerted reaction mechanism remained unchanged. The study demonstrated that the fragmentation reaction of allylic dithiolcarbonates falls into the category of retro-ene type reaction, a thermally allowed pericyclic reaction proceeding through a six-membered nonionic cyclic transition state.

General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides

10.1021/jo5025464

The research focuses on the development of a general method for the preparation of active esters through palladium-catalyzed alkoxycarbonylation of aryl bromides. The study explores the use of various oxygen nucleophiles, including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropanol (HFP), 4-nitrophenol, and N-hydroxyphthalimide, to synthesize active esters with high functional group tolerance and good to excellent isolated yields. The methodology was further extended to access a synthetic precursor to the HIV-protease inhibitor, saquinavir. The experiments involved the use of a Pd catalyst, ligands, and carbon monoxide (CO) under specific conditions to achieve the desired transformations. The analyses used to characterize the products included 1H NMR, 13C NMR, 19F NMR, and HRMS, providing detailed spectral data to confirm the structures of the synthesized active esters.

Propenyl Carboxamide Derivatives as Antagonists of Platelet Activating Factor

10.1021/jm00172a029

This research aimed to develop a series of propenyl carboxamide derivatives as antagonists of Platelet Activating Factor (PAF), a phospholipid mediator involved in allergic and inflammatory diseases. The researchers synthesized and evaluated these compounds, which were conformationally constrained analogues of potent aryl-pentadienecarboxamides. The chemicals used in the synthesis included various aldehydes,(carbomethoxymethylene)triphenylphosphorane, sodium hydroxide, dicyclohexylcarbodiimide, 4-nitrophenol, and specific amines, among others. The research concluded that the position of methoxy groups and the nature of the linking unit "A" significantly influenced the oral bioavailability and activity of the compounds, providing valuable insights for the design of PAF antagonists.