3694-54-0

Upstream product

• 5156-98-9 diethyl phenylphosphoramidite 
• 38568-76-2 N-aniline 
• 141-52-6 sodium ethanolate 
• 62-53-3 aniline 
• 2524-04-1 diethyl phosphorochloridothioate 

Downstream Products

• 2404-05-9 O,O-diethyl S-methyl phosphorothioate 
• 1224851-31-3 C₁₃H₂₁ClNO₂PS 
• 1224851-32-4 C₁₄H₂₃BrNO₂PS 
• 1445-38-1 diethyl phenylphosphoramidate 

Relevant academic research and scientific papers

Kinetics and mechanism of anilinolyses of aryl methyl and aryl propyl chlorothiophosphates in acetonitrile

Nucleophilic substitution reactions of Y-aryl methyl (8) and Y-aryl propyl (10) chlorothiophosphates with substituted anilines and deuterated anilines are investigated kinetically in acetonitrile at 55.0 °C. A concerted mechanism is proposed for 8 based o

Kinetics and mechanism of anilinolyses of ethyl methyl, ethyl propyl and diisopropyl chlorothiophosphates in acetonitrile

Nucleophilic substitution reactions of ethyl methyl (2), ethyl propyl (4) and diisopropyl (7) chlorothiophosphates with substituted anilines and deuterated anilines are investigated kinetically in acetonitrile at 55.0 oC. A concerted mechanism is proposed based on the selectivity parameters. The deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.66-0.99) with 2, primary normal and secondary inverse (kH/ kD = 0.78-1.19) with 4, and primary normal (kH/kD = 1.06-1.21) with 7. The primary normal and secondary inverse DKIEs are rationalized by frontside attack involving hydrogen bonded, four-center-type transitionstate, and backside attack involving in-line-type transition state, respectively. The anilinolyses of ten chlorothiophosphates are examined based on the reactivity, steric effect of the two ligands, thio effect, reactionmechanism, DKIE and activation parameter.

Kinetics and mechanism of the anilinolysis of dimethyl and diethyl chloro(thiono)phosphates

The deuterium kinetic isotope effects (KIEs) involving deuterated aniline nucleophiles (XC6H4ND2) are reported for the reactions of dimethyl chlorophosphate (1), dimethyl chlorothionophosphate (2), diethyl chlorophosphate

Generation of ethyl metathiophosphate by thermal fragmentation of O-ethyl N-substituted phosphoramidothioates

O-Ethyl N-1-adamantylphosphoramidothioate was synthesized and found to fragment on heating in inert solvents to form the pyrophosphate AdNHP(S)(OEt)OP(S)(OEt)OH. The proposed mechanism involves an elimination of the amine portion with release of ethyl metathiophosphate (EtOP(S)O), as was confirmed in previous work for the comparable structure with oxygen. This transient compound then phosphorylates the starting phosphoramidothioate. O-Ethyl N,N-diethylphosphoramidothioate was also synthesized, and while it gave a similar pyro compound on heating, the reaction mixture was more complex. Both phosphoramidothioates, however, served effectively as thiophosphorylating agents toward alcohols, a silanol, and the silanol groups on the surface of silica gel. Exploratory experiments showed that these phosphoramidothioates also could thiophosphorylate the OH group of a monoester of phosphoric acid, as well as that of phosphinic acids, forming anhydrides with the partial structure.

THIONO COMPOUNDS. 8. MUTAGENIC ACTIVITY OF REPRESENTATIVE AMIDES OF THIOPHOSPHORIC ACID

Amides of thiophosphoric acid were studied, in order to initiate correlations of mutagenicity with structure, by use of a modified Ames assay.Representative thiophosphoramides of the structure (XArNH)3PS were not mutagenic, irrespective of whether X was a reference hydrogen atom, an electron-withdrawing, or an electron-donating group.One phosphoramidothioate of the structure (2,4-X2ArNH)P(S)(OCH2CH3)2 effected base-pair mutation when X was F (but not when X was CH3), when S-9 liver homogenate with exogenous NADP was used; when X was H, only inconsistent mutagenic activity following metabolic activation was observed even at concentrations near those that produced acute cellular toxicity.Mutagenicity of these N-arylamides thus appears to follow guidelines concluded for esters, (RO)3PS, i.e. that mutagenesis is most probable when two groups are small enough to permit nucleophilic attack by a biomacromolecule on the electrophilic phosphorus atom.That the third group should be electron withdrawing again seems important although it need not be a good leaving group.An alkyl thionamide, 3PS, resembled the oxygen counterpart, 3PO, to which it probably is biotransformed, in being only marginally mutagenic.We conclude that the hazard of mutagenesis is likely to be less with amides than with esters of thiophosphoric acid and that most of the representative thioamides tested are unlikely to pose serious mutagenic hazards. - Key Words: Ames assay, base-pair mutation, mutagenesis, phosphoramidothioate, thionamide, thiophosphoramide