15959-01-0

Basic information

• Product Name: Thiophosphorsaeure-O,O-diethyl-O-methylester
• Synonyms: Thiophosphorsaeure-O,O-diethyl-O-methylester
• CAS NO: 15959-01-0
• Molecular Weight: 184.196
• Mol File: 15959-01-0.mol

Chemical Properties

• CAS DataBase Reference: Thiophosphorsaeure-O,O-diethyl-O-methylester(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophosphorsaeure-O,O-diethyl-O-methylester(15959-01-0)
• EPA Substance Registry System: Thiophosphorsaeure-O,O-diethyl-O-methylester(15959-01-0)

Safety Data

• Hazardous Substances Data: 15959-01-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 333-41-5 `Diazinon` 
• 2465-65-8 O,O'-diethyl thiophosphoric acid 
• 6257-10-9 N,N'-dicyclohexyl-O-methyl isourea 
• 59425-37-5 N-Phenyl-N'-cyanformamidin 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 

Relevant articles and documents

An ortho-palladated dimethylbenzylamine complex as a highly efficient turnover catalyst for the decomposition of P=S insecticides. Mechanistic studies of the methanolysis of some P=S-containing phosphorothioate triesters

An ortho-palladated complex Pd(dmba)(py)(OTf) (9), or Pd(N,N- dimethylbenzylamine)(pyridine)-(trifluoromethanesulfonate), was synthesized and its solution properties in methanol studied as a function of s spH. In neutral solution the triflate dissociates from the complex to give a dominant form Pd(dmba)(py)(HOCH3), and in acid the pyridine dissociates to give Pyr-H+ and Pd(dmba)(HOCH3)(HOCH 3). Under basic conditions, Pd(dmba)(py)(HOCH3) ionizes to give Pd(dmba)(py)(-OCH3) from which the pyridine can dissociate to yield a mixture of a bis-methoxy-bridged dimer (Pd(dmba)( -OCH3))2 (15-dimer), and its monomer Pd(dmba)(HOCH3)-(-OCH3). Kinetic studies under buffered conditions reveal that 9 is an effective catalyst for the methanolysis of fenitrothion and other P=S pesticides. The active form of the catalyst is a basic one having one associated methoxide generated with an apparent sspKa of 10.8. Analysis of the change in the UV/vis spectrum as a function of sspH generates a spectrophotometric ssKa of 10.8 ±0.1. This catalytic system is shown to promote the methanolysis of fenitrothion (3), diazinon (4), quinalphos (5), coumaphos (10) and dichlofenthion (11) at 0.05 mol dm-3 triethyl amine buffer, sspH 10.8, 25°C, under turnover conditions where the [phosphorothioate]/[9] ratio is 48.6, 13.4, 13.4, 18.6, and 48.6 respectively. In all cases, the products were derived from displacement of the leaving group by methoxide, the second-order turnover rate constants being 36.9, 0.45, 0.12, > 146.7 and 44.3 dm 3 mol-1 s-1 respectively. An associative mechanism for the catalyzed methanolysis of the P=S pesticides is proposed where a transiently coordinated S=P substrate is intramolecularly attacked by the PdII-coordinated methoxide. The Royal Society of Chemistry 2005.

A New, Efficient Synthesis of Thioloesters

The reaction between phosphorothioic and thiocarboxylic acids and O-alkyl-N,N-dicyclohexylisoureas has been found to give the corresponding phosphorothiolates and thiolocarboxylates in high yields (65-95percent), providing a new method for the thiophosphorylation and thiocarboxylation of alcohols.