64131-85-7

Basic information

• Product Name: O,O,O-tris(4-nitrophenyl) thiophosphate
• Synonyms: O,O,O-tris(4-nitrophenyl) thiophosphate;O,O,O-Tris-(4-nitrophenyl)-thiop;Thiophosphoric acid tris(4-nitrophenyl) ester;Thiophosphoric acid=O,O,O-tris(p-nitrophenyl) ester
• CAS NO: 64131-85-7
• Molecular Formula: C₁₈H₁₂N₃O₉PS
• Molecular Weight: 477.341341
• EINECS: 264-697-5
• Mol File: 64131-85-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 636.6°C at 760 mmHg
• Flash Point: 338.8°C
• Appearance: /
• Density: 1.584g/cm³
• Vapor Pressure: 2.06E-15mmHg at 25°C
• Refractive Index: 1.685
• CAS DataBase Reference: O,O,O-tris(4-nitrophenyl) thiophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: O,O,O-tris(4-nitrophenyl) thiophosphate(64131-85-7)
• EPA Substance Registry System: O,O,O-tris(4-nitrophenyl) thiophosphate(64131-85-7)

Safety Data

• Hazardous Substances Data: 64131-85-7(Hazardous Substances Data)

Usage

General Description

O,O,O-tris(4-nitrophenyl) thiophosphate is a chemical compound that is commonly used as an inhibitor of the enzyme acetylcholinesterase, which plays a vital role in the nervous system. It is a potent organophosphate compound that is often used in research and industrial applications. Due to its ability to inhibit acetylcholinesterase, O,O,O-tris(4-nitrophenyl) thiophosphate has toxic effects on the nervous system and can cause symptoms of cholinergic toxicity, such as muscle weakness, respiratory issues, and potential loss of consciousness. O,O,O-tris(4-nitrophenyl) thiophosphate is considered to be hazardous and should be handled with extreme caution in laboratory settings.

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

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

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) 
• 7508-73-8 O-ethyl O,O-di(4-nitrophenyl)thiophosphate 
• 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> 

Relevant articles and documents

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.

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.