31464-99-0

Basic information

• Product Name: N-Methylamidothiophosphoric acid O,O-dimethyl ester
• Synonyms: N-Methylamidothiophosphoric acid O,O-dimethyl ester
• CAS NO: 31464-99-0
• Molecular Formula: C₃H₁₀NO₂PS
• Molecular Weight: 155.16
• Mol File: 31464-99-0.mol

Chemical Properties

• Boiling Point: 55 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 1.178±0.06 g/cm3(Predicted)
• PKA: 1.08±0.70(Predicted)
• CAS DataBase Reference: N-Methylamidothiophosphoric acid O,O-dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylamidothiophosphoric acid O,O-dimethyl ester(31464-99-0)
• EPA Substance Registry System: N-Methylamidothiophosphoric acid O,O-dimethyl ester(31464-99-0)

Safety Data

• Hazardous Substances Data: 31464-99-0(Hazardous Substances Data)

Upstream product

• 2524-03-0 dimethyl chlorothiophosphate 
• 74-89-5 methylamine 
• 593-51-1 methylamine hydrochloride 

Downstream Products

• 123269-09-0 dimethyl N-benzoyl-N-methylphosphoramidothionate 
• 65960-94-3 N,N-dimethyl O,S-dimethyl phosphoramidothioate 
• 65960-92-1 N,O,S-Trimethyl-phosphoramidothiolat 

Relevant articles and documents

Synthesis, spectroscopic characterization and structure-activity relationship of some phosphoramidothioate pesticides

In this work, some phosphoramidothioates (PATs) with the general formula of (CH3O)2P(S)X and (CH3O)(CH3S)P(O)X, where, X = NH2 (1 & 6), NH(CH3) (2 & 7), N(CH3)2 (3 & 8), N(Et)2 (4 & 9), (CH3CH2O)2P(S)NH(CH3) (5) and (CH3CH2O)(CH3CH2S)P(O)NH(CH 3) (10), were synthesized and characterized by 31P, 31P{1H}, 13C and 1H NMR spectroscopy. The ability of the compounds to inhibit AChE was predicted by PASS software (version 1.193). They were also experimentally evaluated by a modified Ellman's assay. The structure-activity relationship (SAR) between IC50 and some physico-chemical properties such as lipophilicity (logP), electronic and steric effects of the compounds was studied. The logP values were experimentally determined by the shake-flask (gas chromatography) method. Inhibitory potency for the compounds 1-10 was 1 (3.38 mM) > 2 (3.97 mM) > 3 (4.75 mM) > 4 (6.00 mM) > 5 (5.51 mM) > 6 (0.07 mM) > 7 (0.23 mM) > 8 (0.39 mM) > and 9 (0.55 mM) > 10 (0.51 mM), respectively. IC50 and logP parameters of the P=O moiety were more than the P=S moiety in PAT analogues.

A New Route to N-Monosubstituted Thioamides Utilizing Phosphoramidothionates as Reagents for the Thioamidation of Carboxylic Acids

Several N-monosubstituted thioamides have been synthesized from the corresponding carboxylic acid chlorides and primary amines by a new procedure.The procedure utilizes a commercially available and inexpensive organophosphorus reagent (dimethyl chlorothiophosphate) to derivatize the amine, form the carboxamide bond, and accomplish the thionation of the carbonyl by an intramolecular rearrangement.The phosphoryl group is then cleaved from the resulting thiocarbonyl phosphoryl mixed imide by a simple hydrolysis.Thioamides (RCSNHR') containing a variety of functionality(R= simple alkyl, phenyl, bulky alkyl, cycloalkylalkyl, α,β-unsaturated, and alkyl with remote keto, ester, or amide carbonyl groups; R'= methyl, benzyl, allyl) have been prepared by this method in generally high overall yields (50-80 percent).Competing thionation of remote carbonyl groups or epimerization of a chiral center containing a proton α to a ketone group was not observed.