5075-13-8

Usage

InChI:InChI=1/C8H10ClOPS/c1-2-10-11(9,12)8-6-4-3-5-7-8/h3-7H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 3497-00-5 phenylthiophosphonic acid dichloride 
• 6230-93-9 (+)-O-ethyl-phenyl-thiophosphonic acid 
• 6230-93-9 (-)-O-ethyl-phenyl-thiophosphonic acid 
• 70269-57-7 (R)_P(+)-O-ethyl phenylphosphonothioic acid 
• 67964-17-4 (S)_P(-)-O-ethyl phenylphosphonothioic acid 

Downstream Products

• 99169-29-6 aziridin-1-yl-phenyl-thiophosphinic acid O-ethyl ester 
• 71091-05-9 phenyl-dithiophosphonic acid O-ethyl ester-S-(2-ethylsulfanyl-ethyl ester) 
• 2104-64-5 EPN 
• 35279-97-1 Phenyl-phosphonothioic acid O-((Z)-2-cyano-1-phenyl-vinyl) ester O-ethyl ester 
• 35276-73-4 Phenyl-phosphonothioic acid O-((Z)-2-cyano-1-p-tolyl-vinyl) ester O-ethyl ester 
• 35276-72-3 Phenyl-phosphonothioic acid O-[(Z)-1-(4-chloro-phenyl)-2-cyano-vinyl] ester O-ethyl ester 
• 35276-65-4 Phenyl-phosphonothioic acid O-[(Z)-2-cyano-1-(4-methoxy-phenyl)-vinyl] ester O-ethyl ester 
• 40401-97-6 C₁₀H₁₅N₂O₂PS₂ 
• 37862-84-3 Phenylthiophosphonsaeureanhydrid 
• 93180-24-6 C₉H₁₀NOPS 

Relevant academic research and scientific papers

Kinetics and mechanism of the anilinolysis of o-ethyl phenyl phosphonochloridothioate in acetonitrile

The nucleophilic substitution reactions of O-ethyl phenyl phosphonochloridothioate with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) are kinetically investigated in acetonitrile at 55.0 °C. The deuterium kinetic isotope effects (DKIEs) invariably increase from a secondary inverse DKIE (kH/kD = 0.93) to a primary normal DKIE (kH/kD = 1.28) as the substituent of nucleophile (X) changes from electron-donating to electron-withdrawing. These can be rationalized by the gradual transition state (TS) variation from a backside to frontside attack. A concerted SN2 mechanism is proposed. A trigonal bipyramidal TS is proposed for a backside attack while a hydrogen-bonded, four-center-type TS is proposed for a frontside attack.

Stereochemistry and Reactions of Aziridinylphosphinothionates Derived from Amino Acids

Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphosphonothionates and 1-bromo-2-alkanamines derived from leucine or valine.The aziridine ring was opened by the action of some nucleophiles.Refluxing the aziridinylphosphinethionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates.The reaction mechanism was discussed eith stereochemical considerations.The insecticidal activity of the products was also examined.

SILICON-PHOSPHORUS ANALOGIES. PARTICIPATION OF EXTERNAL NUCLEOPHILES TO ACTIVATED PROCESSES OF RACEMIZATION AND HYDROLYSIS OF CHLOROPHOSPHONO DERIVATIVES

Kinetic and stereochemical studies show nucleophilic assistance by dimethylformamide (DMF), dimethylacetamide (DMA), hexamethylphosphotriamide (HMPT) and N-methylimidazole (NMI) in racemization and solvolysis of menthylchloro(phenyl)phosphonate, 1a, and O-ethylchloro(phenyl)thiophosphonate, 2.Similar orders of nucleophilic reactivity (Nu = NMI >> HMPT > DMF> DMA), and identical rate laws (vrac = k 2 and vH2O = k') are consistent with a common mechanism, governed by entropy (-60 u.e/= -40 u.e.).Analogies between reaction mechanisms at silicon and phosphorus are clearly evidenced.A two step process, involving rate-determining attack on a pentacoordinate complex is discussed.

NUCLEOPHILIC ASSISTANCE IN THE FORMATION OF PYROPHOSPHONATE: EFFECTIVE SIDE-REACTION OF HALOGENOPHOSPHORUS COMPOUNDS WITH WATER IN APROTIC SOLVENTS

Aside from racemization and direct solvolysis of halogenophosphonates, nucleophilic assistance by dimethylformamide, hexamethylphosphotriamide, N-methylimidazole, pyridine or triethylphosphite in wet solvents brings about P-O-P bond formation.The nucleophiles are not directly involved in the chemical reaction.The oxygen atom originates from H2O.The reaction does not nevertheless take place via consecutive coupling reaction between preliminary formed phosphonic acid and a second molecule of phosphonic chloride.As proposed in the case of activated racemization and hydrolysis of halogenophosphonates, the mechanistic pathway envisaged involves nucleophilic assistance to dimerization, prior to hydrolysis.In the course of the dynamic stereochemical study of alkyl chloro phenylphosphonates or alkyl chloro phenylthiophosphonates in the presence of nucleophilic agents (dimethylormamide(DMF), hexamethylphosphotriamide(HMPT), N-methylimidazole (NMI), pyridine or triethylphosphite), we have mentioned secondary reactions giving variable amounts of oxo (or thio) pyrophosphonic esters, with P-O-P linkages.Ester formation, although unimportant in the direct hydrolysis, can dominate in nucleophilic catalysed racemization performed in wet solvents.In the present note, we describe quantitative and stereochemical experiments designed to elucidate the formation of such compounds.