4-Nitrophenyl diphenyl phosphate

Base Information

• Chemical Name: 4-Nitrophenyl diphenyl phosphate
• CAS No.: 10359-36-1
• Molecular Formula: C18H14 N O6 P
• Molecular Weight: 371.286
• Hs Code.: 2919900090
• DSSTox Substance ID: DTXSID60145926
• Nikkaji Number: J315.187E
• Wikidata: Q83010632
• ChEMBL ID: CHEMBL278353
• Mol file: 10359-36-1.mol

Synonyms:p-nitrophenyl diphenyl phosphate;p-NPDPP cpd

Chemical Property of 4-Nitrophenyl diphenyl phosphate

Chemical Property:

• Vapor Pressure: 4.51E-08mmHg at 25°C
• Boiling Point: 456.1°Cat760mmHg
• Flash Point: 229.6°C
• PSA: 111.39000
• Density: 1.376g/cm³
• LogP: 5.34320
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 371.05587416
• Heavy Atom Count: 26
• Complexity: 466

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC=C(C=C3)[N+](=O)[O-]

Technology Process of 4-Nitrophenyl diphenyl phosphate

There total 7 articles about 4-Nitrophenyl diphenyl phosphate 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: 98.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + chlorophosphoric acid diphenyl ester (2524-64-3) → 4-nitro-phenyl diphenyl phosphate (10359-36-1)

Guidance literature:

With titanium tetrachloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol026618q

Reference yield: 75.0%

1-dichlorophosphoryloxy-4-nitro-benzene (777-52-6) + phenol (108-95-2,27073-41-2) → 4-nitro-phenyl diphenyl phosphate (10359-36-1)

Guidance literature:

With triethylamine; In chloroform; at 20 ℃; for 4h; Cooling with ice; Inert atmosphere;

DOI:10.1002/chem.201101926

Reference yield: 56.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + (2-oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diphenyl ester (681035-22-3) → 4-nitro-phenyl diphenyl phosphate (10359-36-1)

Guidance literature:

With N,N'-bis(benzyliden)ethylendiamine; copper(II) bis(trifluoromethanesulfonate); triethylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1021/ol051104n

upstream raw materials:

4-nitro-phenol

chlorophosphoric acid diphenyl ester

diphenyl hydrogen phosphate

lithium 4-nitrophenolate

Downstream raw materials:

diphenyl (1H-imidazol-1-yl)phosphonate

Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester

p-nitrophenolate

phosphoric acid triphenyl ester

Refernces

Substituted o-Iodoso- and o-Iodoxybenzoic Acids: Synthesis and Catalytic Activity in the Hydrolysis of Active Phosphorus Esters and Related Systems

10.1021/jo00252a017

The research focuses on the synthesis and catalytic activity of 2-iodoso- and 2-iodoxybenzoic acids, which contain various substituents such as alkyl, alkyloxy, nitro, carboxyl, and water-solubilizing groups. The purpose of this study was to determine the influence of these substituents on the rates of hydrolysis of active phosphorus esters, including p-nitrophenyl diphenyl phosphate (PNPDPP), p-nitrophenyl isopropylphenylphosphinate (NPIPP), and p-nitrophenyl hexanoate (PNPH), in the presence of cetyltrimethylammonium chloride (CTAC). The research concluded that all synthesized compounds act as true catalysts, with their catalytic activity increasing with higher catalyst concentrations. Notably, 2-iodoxybenzoic acids showed 60-110% of the activity of their 2-iodosobenzoic acid analogues in 0.001 M CTAC. The study found that lipophilic substituents significantly enhanced the catalytic rates, while electron-releasing, -withdrawing, and water-soluble groups had moderate effects. The research also identified that 5-(2-hydroxyethoxy)-2-iodoxybenzoic acid and 5-(alkyloxy)-2-iodosobenzoic and -2-iodoxybenzoic acid derivatives exhibited extraordinary rate enhancements, making these compounds potentially useful as decontaminants for active phosphorus derivatives.