311-45-5

Usage

Chemical Description

Paraoxon and tributyl phosphate are substrates that were used to study the catalytic activity of the phosphotriesterase enzyme.

Uses

Used in Insecticide Industry:
PARAOXON is used as an insecticide for controlling various pests that damage crops and pose a threat to agriculture. Its cholinesterase inhibiting properties make it effective in disrupting the nervous system of insects, leading to their paralysis and death.
Used as a Cholinesterase Inhibitor:
PARAOXON is used as a cholinesterase inhibitor in research and pharmaceutical applications. It is a potent inhibitor of the enzyme acetylcholinesterase, which is essential for the proper functioning of the nervous system. By inhibiting this enzyme, PARAOXON can be used to study the effects of cholinesterase inhibition on various biological processes.
Used in Paraoxonase (PON) Activity Assay:
PARAOXON-ethyl has been used as a substrate in paraoxonase (PON) activity assays. PON is an enzyme that plays a crucial role in the detoxification of various xenobiotics, including organophosphates like PARAOXON. By using PARAOXON-ethyl as a substrate, researchers can study the activity and efficiency of PON in detoxifying harmful compounds.
Used as a Lipase Inhibitor in Pharmaceutical Research:
PARAOXON has been used as a lipase inhibitor to study the effects of anacetrapib on homotypic transfer from high-density lipoprotein L3 (HDL3) to HDL2 in vivo. This application helps researchers understand the role of lipase in lipid metabolism and the potential therapeutic effects of drugs like anacetrapib on lipid-related disorders.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 3359, 1990 DOI: 10.1016/S0040-4039(00)89065-6

Reactivity Profile

Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Fire Hazard

Flash point data for PARAOXON are not available; however, PARAOXON is probably combustible.

Biochem/physiol Actions

Potent irreversible acetylcholinesterase inhibitor

Safety Profile

A deadly poison by ingestion,intraperitoneal, intravenous, subcutaneous, intramuscular,and parenteral routes. Mutation data reported. Humansystemic effects: coma, convulsions, miosis. Acholinesterase inhibitor. An insecticide. When heated todecompos

Potential Exposure

An organophosphate insecticide. Has been used as a medication.

Incompatibilities

Keep away from alkaline materials and strong oxidizers. Contact with oxidizers can cause the release of toxic oxides of phosphorus. May react violently with antimony(V) pentafluoride. Incompatible with lead diacetate, magnesium, silver nitrate. In the presence of strong reducing agents such as hydrides, organophosphates form highly toxic and flammable phosphine gas.

Waste Disposal

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C6H6NO6P.C4H10/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12;1-3-4-2/h1-4H,(H2,10,11,12);3-4H2,1-2H3

Upstream product

• 100-02-7 4-nitro-phenol 
• 107-49-3 Tetraethyl pyrophosphate 
• 777-52-6 1-dichlorophosphoryloxy-4-nitro-benzene 
• 64-17-5 ethanol 
• 2510-86-3 O,O-diethyl O-phenyl phosphate 
• 814-49-3 diethyl chlorophosphate 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 762-04-9 phosphonic acid diethyl ester 
• 56-38-2 parathion 
• 1124-32-9 lithium 4-nitrophenolate 
• 598-02-7 Diethyl phosphate 
• 681035-21-2 (2-oxo-5,5-diphenyl-oxazolidin-3-yl)-phosphonic acid diethyl ester 
• 78-40-0 triethyl phosphate 
• 824-78-2 4-nitrophenol sodium salt 

Downstream Products

• 78-40-0 triethyl phosphate 
• 824-78-2 4-nitrophenol sodium salt 
• 598-02-7 Diethyl phosphate 
• 2870-30-6 sodium diethyl phosphate 
• 27147-79-1 Sodium; cyclopentyl-acetate 
• 100-02-7 4-nitro-phenol 
• 14609-74-6 p-nitrophenolate 
• 48042-47-3 diethyl phosphate 
• 2510-86-3 O,O-diethyl O-phenyl phosphate 
• 330-13-2 mono-p-nitrophenyl phosphate 
• 17659-67-5 ethyl p-nitrophenyl phosphate 
• 867-17-4 diethyl methyl phosphate 
• 1124-31-8 potassium 4-nitrophenolate 
• 1124-32-9 lithium 4-nitrophenolate 

Relevant academic research and scientific papers

Monitoring the phosphorylation of phenol derivatives with diethyl chlorophosphate in liquid-liquid and solid-liquid phase by in situ fourier transform infrared spectroscopy, part II

The reaction of 4-chlorophenol and 4-nitrophenol with diethyl chlorophosphate carried out in a liquid-liquid and solid-liquid two phase system, respectively, was monitored by in situ Fourier transform IR spectroscopy. Copyright Taylor & Francis Group, LLC.

Electrochemical phosphorylation of arenols and anilines leading to organophosphates and phosphoramidates

A practical phosphorylation for generating organophosphates and phosphoramidatesviaelectrochemical dehydrogenative cross-coupling of P(O)H compounds with arenols and anilines is disclosed. This method involves using inorganic iodide salts as both redox catalysts and electrolytes in an undivided cell without the addition of oxidants or bases. A preliminary mechanistic study suggests that radicals are not involved in this process. This method is green and eco-friendly and has good functional group tolerance, high yields and broad substrate scope, with the potential for practical synthesis.

Identification of organophosphorus simulants for the development of next-generation detection technologies

Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.

Quinoline compound as well as preparation method, pharmaceutical composition and application thereof

The invention discloses a compound shown as a general formula I, pharmaceutically acceptable salt or metabolite of the compound, and a preparation method, a pharmaceutical composition and applicationof the compound. The compound shown in the general formula I, the pharmaceutically acceptable salt thereof or the metabolite thereof has a good treatment effect on virus infection, has small toxic andside effects, and can be used for preventing or treating virus infection.

LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates

An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.

P-nitrophenyl phosphate disodium and preparation method thereof

The invention provides p-nitrophenyl phosphate disodium and a preparation method thereof. The preparation method comprises the following steps: 1, enabling p-nitrophenol to react with dialkyl chloridephosphate in the presence of an alkali so as to obtain O,O-dialkyl p-nitrophenyl phosphate; 2, performing an alkyl ester desorption reaction on the O,O-dialkyl p-nitrophenyl phosphate and a compoundwith trimethylsilyl groups so as to obtain O,O-di(trimethylsilyl) p-nitrophenyl phosphate; 3, performing a hydrolysis reaction on the O,O-di(trimethylsilyl) p-nitrophenyl phosphate so as to obtain p-nitrophenyl phosphate; and 4, enabling the p-nitrophenyl phosphate to react with sodium hydroxide, so as to obtain the p-nitrophenyl phosphate disodium. According to the preparation method provided bythe invention, the intermediate product obtained in the step 1 can be purified through vacuum distillation, and byproducts which are hard to remove are not generated in later operation of ether hydrolysis or pH value adjustment, so that the purification difficulty of the product is greatly reduced; and due to selection of the compound with the trimethylsilyl groups, hydrolysis can be implemented thoroughly, and in addition, the system can be clean.

Transition State Analysis of the Reaction Catalyzed by the Phosphotriesterase from Sphingobium sp. TCM1

Organophosphorus flame retardants are stable toxic compounds used in nearly all durable plastic products and are considered major emerging pollutants. The phosphotriesterase from Sphingobium sp. TCM1 (Sb-PTE) is one of the few enzymes known to be able to hydrolyze organophosphorus flame retardants such as triphenyl phosphate and tris(2-chloroethyl) phosphate. The effectiveness of Sb-PTE for the hydrolysis of these organophosphates appears to arise from its ability to hydrolyze unactivated alkyl and phenolic esters from the central phosphorus core. How Sb-PTE is able to catalyze the hydrolysis of the unactivated substituents is not known. To interrogate the catalytic hydrolysis mechanism of Sb-PTE, the pH dependence of the reaction and the effects of changing the solvent viscosity were determined. These experiments were complemented by measurement of the primary and secondary 18-oxygen isotope effects on substrate hydrolysis and a determination of the effects of changing the pKa of the leaving group on the magnitude of the rate constants for hydrolysis. Collectively, the results indicated that a single group must be ionized for nucleophilic attack and that a separate general acid is not involved in protonation of the leaving group. The Br?nsted analysis and the heavy atom kinetic isotope effects are consistent with an early associative transition state with subsequent proton transfers not being rate limiting. A novel binding mode of the substrate to the binuclear metal center and a catalytic mechanism are proposed to explain the unusual ability of Sb-PTE to hydrolyze unactivated esters from a wide range of organophosphate substrates.

Tf2O-Promoted Activating Strategy of Phosphate Analogues: Synthesis of Mixed Phosphates and Phosphinate

A metal-, toxic chloride reagent-free activating strategy of various phosphates has been developed. This method enables the facile synthesis of functional phosphates such as alkyl phosphates, aza phosphates, thiophosphate, and mixed diaryl phosphates. A transient phosphorylpyridin-1-ium species in situ generated from phosphates with Tf2O/pyridine readily undergoes a substitution reaction with diverse nucleophiles to form versatile phosphate compounds.

Diethyl phosphite production from phosphorothioate degradation with molybdenum peroxides and hydrogen peroxide in ethanol

A polystyrene-supported molybdate-peroxide polymer (Mo-Y(s)) destroys phosphorothioate pesticides of the form (ArO)P(=S)(OEt)2 in EtOH under mild oxidative (H2O2) conditions and produces a commodity organophosphate. This is the first report of a metal-based system that successfully degrades the “live” pesticides parathion, diazinon and coumaphos. In addition to the operational advantages of heterogeneous reaction chemistry, the Mo-Y(s) support degrades multiple equivalents of the pesticide in H2O2(aq). Of particular importance is the predominant production of diethyl phosphite, a commodity chemical, from diazinon degradation over Mo-Y(s) in EtOH; no toxic oxon is found. Coumaphos and parathion produce the corresponding oxon which have ΔH? (kcal/mol) of 15.4 (0.5) and 21.7 (0.8), respectively; these activation parameters are consistent with key observations found in the relative amount of coumoxon and paraoxon produced. Finally, a discrete molybdate-peroxide complex is presented as a possible solution model for this heterogeneous reaction.

Mechanisms of degradation of paraoxon in different ionic liquids

Herein, the reactivity and selectivity of the reaction of O,O-diethyl 4-nitrophenyl phosphate triester (Paraxon, 1) with piperidine in ionic liquids (ILs), three conventional organic solvents (COS), and water is studied by 31P NMR, UV-vis, and GC/MS. Three phosphorylated products are identified as follows: O,O-diethyl piperidinophosphate diester (2), O,O-diethyl phosphate (3), and O-ethyl 4-nitrophenyl phosphate diester (4). Compound 4 also reacts with piperidine to yield O-ethyl piperidinophosphate monoester (5). The results show that both the rate and products distribution of this reaction depend on peculiar features of ILs as reaction media and the polarity of COS.