64131-85-7

Usage

Uses

Used in Research Applications:
O,O,O-tris(4-nitrophenyl) thiophosphate is used as a research tool for studying the function and inhibition of acetylcholinesterase enzyme. Its ability to inhibit this enzyme makes it a valuable compound in understanding the role of acetylcholinesterase in the nervous system and the effects of its inhibition.
Used in Industrial Applications:
In industrial settings, O,O,O-tris(4-nitrophenyl) thiophosphate is employed as an acetylcholinesterase inhibitor for various purposes, such as in the development of pesticides or as a component in certain chemical processes. Its potent inhibitory effects on acetylcholinesterase are leveraged to achieve desired outcomes in these applications.
Used in Toxicological Studies:
O,O,O-tris(4-nitrophenyl) thiophosphate is also used in toxicological research to investigate the effects of cholinergic toxicity on the nervous system. This helps in understanding the mechanisms of toxicity and potential countermeasures or treatments for exposure to organophosphate compounds.

InChI:InChI=1/C18H12N3O9PS/c22-19(23)13-1-7-16(8-2-13)28-31(32,29-17-9-3-14(4-10-17)20(24)25)30-18-11-5-15(6-12-18)21(26)27/h1-12H

Upstream product

• 100-02-7 4-nitro-phenol 
• 23485-35-0 tris(p-nitrophenyl)-phosphite 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 124-41-4 sodium methylate 

Downstream Products

• 116035-17-7 thiophosphoric acid O,O'-bis-(4-nitro-phenyl ester); silver-salt 
• 3871-20-3 tris(p-nitrophenyl)phosphate 
• 39004-94-9 thiophosphoric acid O-methyl ester-O',O''-bis-(4-nitro-phenyl ester) 
• 423771-31-7 thiophosphoric acid O-isopropyl ester-O',O''-bis-(4-nitro-phenyl ester) 
• 100-02-7 4-nitro-phenol 
• 72448-65-8 Thiophosphorsaeure-O,O-bis-<4-nitro-phenylester> 
• 7508-73-8 O-ethyl O,O-di(4-nitrophenyl)thiophosphate 

Relevant academic research and scientific papers

Substituent effects on the 31P NMR chemical shifts of arylphosphorothionates

Six tris(aryloxy)phosphorothionates substituted in the para position of the aromatic rings were synthesized and studied by 31P NMR, X-ray diffraction techniques and ab initio calculations at a RHF/6-31G** level of theory, in order to find the main structural factors associated with the δ31P in these compounds. As the electron-withdrawing (EW) ability of the substituents was increased, an 'abnormal' shielding effect on δ31P of the arylphosphorothionates was observed. The analyses of the geometrical properties obtained through both experimental and theoretical methods showed that a propeller-type conformation is preferred for the arylphosphorothionates, except in the case of the tris(O-4-methylphenyl) phosphorothionate, since one of the aromatic rings is not rotated in the same direction as the other two in the solid state. The main features associated with the δ31P NMR of compounds 1-6 were a decrease of the averaged O-P-O angle and mainly the shortening of the PS bond length, which is consistent with an increase of the thiophosphoryl bond order as δ31P values go upfield. On the other hand, comparison of the experimental and calculated bond lengths and bond angles involving α bonded atoms to phosphorus of the six compounds suggested that stereoelectronic interactions of the type nπO-σ*PS, nπO- σ*P-OAr and nπS-σ* P-OAr could be present in the arylphosphorothionates 1-6.

Synthesis of O,O,O-triaryl phosphorothioates and O-aryl phosphorodichloridothioates using poly(ethylene glycol) as a phase transfer catalyst

O,O,O-Triaryl phosphorothioates and O-aryl phosphorodichloridothioates have been prepared in good yields and purity from thiophosphoryl chloride and phenol using poly(ethylene glycol)-400 (PEG-400) as a phase transfer catalyst.

Phase-Transfer-Catalyzed Preparation of Triaryl Phosphorothionates

Triaryl phosphorothionates have been prepared in good yield from thiophosphoryl chloride and three equivalents of a phenol by a phase-transfer-catalyzed process.