2566-26-9

Usage

Uses

Used in Biochemistry and Molecular Biology:
2,4-dinitrophenylphosphate is used as a substrate for the assay of acid or alkaline phosphatase activity. It serves as a colorimetric indicator, changing color to yellow when hydrolyzed by phosphatase enzymes, which aids in measuring enzymatic activity and studying enzyme kinetics.
Used in Pharmaceutical and Specialty Chemicals Production:
2,4-dinitrophenylphosphate is used as an intermediate in the synthesis of other organic compounds, making it a useful component in the production of pharmaceuticals and other specialty chemicals. Its versatility in chemical reactions contributes to the development of new compounds with potential applications in various industries.

InChI:InChI=1/C6H5N2O8P/c9-7(10)4-1-2-6(16-17(13,14)15)5(3-4)8(11)12/h1-3H,(H2,13,14,15)

Upstream product

• 62736-35-0 2,4-Dinitro-phenyl-phosphorsaeuredibenzylester 
• 54436-53-2 O,O-diethyl (2,4-dinitrophenyl) phosphate triester 
• 18962-97-5 bis(2,4-dinitrophenyl)phosphate 
• 51-28-5 2,4-Dinitrophenol 

Downstream Products

• 51-28-5 2,4-Dinitrophenol 
• 80572-53-8 t-butyl phosphate mono N-ethyl diisopropylamine salt 
• 80572-54-9 Phosphoric acid monophenyl ester; compound with ethyl-diisopropyl-amine 
• 20350-26-9 2,4-dinitrophenolate 
• 66391-31-9 dimethyl 2,4-dinitrophenyl phosphate 

Relevant academic research and scientific papers

Preparation of the copper(n) complex of the binucleating hexaaza macrocycle 2,5,8,17,20,23-hexaaza[9.9]paracyclophane and its solution chemistry, hydrolytic activity and acid dissociation kinetics

The binucleating hexaaza macrocycle 2,5,8,17,20,23-hexaaza[9.9]paracyclophane (PEA) and its N-permethylated derivative 2,5,8,17,20,23-hexamethyl-2,5,8,17,20,23-hexaaza[9.9]paracyclophane (Me6PEA) have been prepared. The copper(II) complex of PEA has been prepared and the stability constants of the copper complexes determined in aqueous solution by potentiometric and spectrophotometric methods. The protonation sites of PEA have been identified by NMR titration. The crystal structure of the complex [Cu2(PEA)Cl3]+Cl-·2.6MeCN ·2.9H2O has been determined. The copper centres have an N3C12 donor set with a square pyramidal geometry. The Cu ... Cu distance is 7.02 A. The copper complex catalyses hydrolysis of the phosphotriester 2,4-dinitrophenyl diethyl phosphate (DNPDEP) and the [Cu2(PEA)(OH)2]2 and [Cu2(PEA)(OH)]3+ complexes have been identified as the active species. The acid catalysed dissociation of the copper complex has been studied by stopped-flow methods. The reaction is monophasic and displays saturation kinetics at high acidities. The Royal Society of Chemistry 2001.

Synthesis, characterization, hydrolase and catecholase activity of a dinuclear iron(III) complex: Catalytic promiscuity

Abstract Herein, we report the synthesis and characterization of the new di-iron(III) complex [(bbpmp)(H2O)(Cl)FeIII(μ-Ophenoxo)FeIII(H2O)Cl)]Cl (1), with the symmetrical ligand 2,6-bis{[(2-hydroxyben

Synthesis, structure, magnetism, and hydrolase and catecholase activity of a new trinuclear copper(II) complex

In this paper we report the synthesis of the new multidentate N,O-donor ligand H3L-2pyald = (N,N′-bis-(2-pyridylmethyl)-(2-hydroxy-3-carbonyl-5-methylbenzyl)-1,3-propanediamine-2-ol) and its first trinuclear copper(II) complex, [Cu3(

Cu(ii) complexes with tridentate sulfur and selenium ligands: catecholase and hydrolysis activity

Two new copper(ii) mononuclear complexes (CSe and CS) were synthesized and characterized by the following techniques: X-ray crystallography, elemental analysis, IR, EPR and UV-vis spectroscopies, conductimetric analysis and mass spectrometry. The crystall

Synthesis and enhanced DNA cleavage activities of bis-tacnorthoamide derivatives

A new metal-free DNA cleaving reagent, bis-tacnorthoamide derivative 1 with two tacnorthoamide (tacnoa) units linked by a spacer containing anthraquinone, has been synthesized from triazatricyclo[5.2.1.04,10]decane and characterized by NMR and mass spectrometry. For comparison, the corresponding compounds mono-tacnorthoamide derivative 2 with one tacnorthoamide unit and 6 with two tacnorthoamide units linked by an alkyl (1,6-hexamethylene) spacer without anthraquinone have also been synthesized. The DNA-binding property investigated via fluorescence and CD spectroscopy suggests that compounds 1 and 2 have an intercalating DNA binding mode, and the apparent binding constants of 1, 2 and 6 are 1.3 × 107 M-1, 0.8 × 10 7 M-1 and 8 × 105 M-1, respectively. Agarose gel electrophoresis was used to assess plasmid pUC19 DNA cleavage activity promoted by 1, 2, 6 and parent tacnoa under physiological conditions, which gives rate constants kobs of 0.2126 ± 0.0055 h-1, 0.0620 ± 0.0024 h-1, 0.040 ± 0.0007 h-1 and 0.0043 ± 0.0002 h-1, respectively. The 50-fold and 15-fold rate acceleration over parent tacnoa is because of the anthraquinone moiety of compound 1 or 2 intercalating into DNA base pairs via a stacking interaction. Moreover, DNA cleavage reactions promoted by compound 1 give 5.3-fold rate acceleration over compound 6, which further demonstrates that the introduction of anthraquinone results in a large enhancement of DNA cleavage activity. In particular, DNA cleavage activity promoted by 1 bearing two tacnoa units is 3.3 times more effective than 2 bearing one tacnoa unit and the DNA cleavage by compound 1 was achieved effectively at a relatively low concentration (0.03 mM). This dramatic rate acceleration suggests the cooperative catalysis of the two positively charged tacnoa units in compound 1. The radical scavenger inhibition study and ESI-MS analysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) and adenylyl(3′-5′) phosphoadenine (APA) cleavage in the presence of compound 1 suggest the cleavage mechanism would be via a hydrolysis pathway by cleaving the phosphodiester bond of DNA.

Unsymmetrical dizinc complexes as models for the active sites of phosphohydrolases

The unsymmetrical dinucleating ligand 2-(N-isopropyl-N-((2-pyridyl)methyl) aminomethyl)-6-(N-(carboxylmethyl)-N-((2-pyridyl)methyl)aminomethyl) -4-methylphenol (IPCPMP or L) has been synthesized to model the active site environment of dinuclear metallohydrolases. It has been isolated as the hexafluorophosphate salt H4IPCPMP(PF6)2· 2H2O (H4L), which has been structurally characterized, and has been used to form two different Zn(ii) complexes, [{Zn2(IPCPMP) (OAc)}2][PF6]2 (2) and [{Zn2(IPCPMP) (Piv)}2][PF6]2 (3) (OAc = acetate; Piv = pivalate). The crystal structures of 2 and 3 show that they consist of tetranuclear complexes with very similar structures. Infrared spectroscopy and mass spectrometry indicate that the tetranuclear complexes dissociate into dinuclear complexes in solution. Potentiometric studies of the Zn(ii):IPCPMP system in aqueous solution reveal that a mononuclear complex is surprisingly stable at low pH, even at a 2:1 Zn(ii):L ratio, but a dinuclear complex dominates at high pH and transforms into a dihydroxido complex by a cooperative deprotonation of two, probably terminally coordinated, water molecules. A kinetic investigation indicates that one of these hydroxides is the active nucleophile in the hydrolysis of bis(2,4-dinitrophenyl)phosphate (BDNPP) enhanced by complex 2, and mechanistic proposals are presented for this reaction as well as the previously reported transesterification of 2-hydroxypropyl p-nitrophenyl phosphate (HPNP) promoted by Zn(ii) complexes of IPCPMP.