86801-05-0

Basic information

• Product Name: O-ethyl-O-phenyl-phosphorochloridothioate
• CAS NO: 86801-05-0
• Molecular Weight: 236.659
• Mol File: 86801-05-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-ethyl-O-phenyl-phosphorochloridothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O-ethyl-O-phenyl-phosphorochloridothioate(86801-05-0)
• EPA Substance Registry System: O-ethyl-O-phenyl-phosphorochloridothioate(86801-05-0)

Safety Data

• Hazardous Substances Data: 86801-05-0(Hazardous Substances Data)

Upstream product

• 1498-64-2 O-ethyl dichlorothiophosphate 
• 108-95-2 phenol 
• 32345-29-2 O,O-diethyl-O-phenyl phosphorothioate 
• 64-17-5 ethanol 
• 18961-96-1 O-phenylphosphorodichloridothioate 

Downstream Products

• 41315-37-1 C₉H₁₄NO₃PS 
• 69322-82-3 [1-Amino-eth-(Z)-ylidene]-thiophosphoramidic acid O-ethyl ester O'-phenyl ester 
• 33529-26-9 C₁₅H₁₉N₂O₄PS₂ 
• 160422-77-5 O-ethyl-O-phenylisothiocyanatothiophosphate 
• 1381809-23-9 C₂₈H₂₅N₂O₇PS 
• 1240409-91-9 O-ethyl, O-phenyl, O-(Z-[1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethylidene]amino) phosphorothioate 
• 135492-39-6 (5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O-ethyl ester O-phenyl ester 
• 33529-25-8 C₉H₁₅N₂O₄PS₂ 

Relevant articles and documents

Kinetics and mechanism of the aminolysis of aryl ethyl chloro and chlorothio phosphates with anilines

The reactions of ethyl Y-phenyl chloro (1) and chlorothio (2) phosphates with X-anilines in acetonitrile at 55.0 °C are studied kinetically and theoretically. Kinetic results yield the primary kinetic isotope effects (k H/kD = 1.07-1.80 and 1.06-1.27 for 1 and 2, respectively) with deuterated aniline (XC6H4ND2) nucleophiles, and the cross-interaction constants ρXY = -0.60 and -0.28 for 1 and 2, respectively. A concerted mechanism involving a partial frontside attack through a hydrogen-bonded, four-center-type transition state is proposed. The large ρX (ρnuc = -3.1 to -3.4) and βX (βnuc = 1.1-1.2) values seem to be characteristic of the anilinolysis of phosphates and thiophosphates with the Cl leaving group. Because of the relatively large size of the aniline nucleophile, the degree of steric hindrance could be the decisive factor that determines the direction of the nucleophilic attack to the phosphate and thiophosphate substrates with the relatively small-sized Cl leaving group. This journal is The Royal Society of Chemistry.

A new convenient synthesis of phosphoro(-no)chloridothionates

A general procedure for synthesis of phosphoro(-no)chlorides, particularly unsymmetrical ones, has been developed. The method involves the dealkylation of O,O-dialkyl phosphoro(-no)thionates 1 with dimethylamine and the chlorination of O-alkyl ammonium phosphoro(-no)thioates 2 using phosphorus oxychloride as a chlorinating agent.