22608-53-3

Basic information

• Product Name: O,S,S-trimethyl phosphorodithioate
• Synonyms: O,S,S-trimethyl phosphorodithioate;O,S,S-TRIMETHYLPHOSPHOROTHIOLATE;O,S,S-TRI-METHYLPHOSPHORODIOTHIOATE;TRIMETHYLPHOSPHORODITHIOATE;Phosphorodithioic acid O,S,S-trimethyl ester
• CAS NO: 22608-53-3
• Molecular Formula: C₃H₉O₂PS₂
• Molecular Weight: 172.21
• Mol File: 22608-53-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 222.6°C at 760 mmHg
• Flash Point: 88.4°C
• Appearance: /
• Density: 1.2500
• Vapor Pressure: 0.15mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: O,S,S-trimethyl phosphorodithioate(CAS DataBase Reference)
• NIST Chemistry Reference: O,S,S-trimethyl phosphorodithioate(22608-53-3)
• EPA Substance Registry System: O,S,S-trimethyl phosphorodithioate(22608-53-3)

Safety Data

• Hazardous Substances Data: 22608-53-3(Hazardous Substances Data)

Usage

General Description

O,S,S-trimethyl phosphorodithioate is a highly toxic organophosphorus compound used as a pesticide, insecticide, and acaricide. It is a colorless to slightly yellow liquid with a strong odor, and it is not soluble in water but can be dissolved in organic solvents. This chemical works by inhibiting cholinesterase, an enzyme responsible for breaking down the neurotransmitter acetylcholine. Inhibition of this enzyme leads to an accumulation of acetylcholine in the nerve synapses, causing overstimulation of the nervous system and ultimately leading to paralysis and death in insects and other pests. Due to its high toxicity and potential for environmental harm, the use of O,S,S-trimethyl phosphorodithioate is heavily regulated and restricted in many countries. It is important to handle this chemical with extreme caution and ensure proper safety measures are in place during its use.

InChI:InChI=1/C3H9O2PS2/c1-5-6(4,7-2)8-3/h1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 22608-55-5 S,S-dimethyl phosphorodithioate potassium salt 
• 77-78-1 dimethyl sulfate 
• 26377-29-7 sodium O,O-dimethyl phosphorodithioate 
• 74-83-9 methyl bromide 

Downstream Products

• 69078-99-5 cis-Propenyl O,O'-Dimethyl Dithiophosphate 
• 5514-35-2 isopropyl methyl phosphonate 

Relevant articles and documents

S-methylation of O,O-dialkyl phosphorodithioic acids: O,O,S-trimethyl phosphorodithioate and phosphorothiolate as metabolites of dimethoate in mice

O,O,S-Trimethyl phosphorodithioate and phosphorothiolate [(MeO)2P(S)SMe and (MeO)2P-(O)SMe, respectively] are known from earlier studies to be impurities, delayed toxicants, and detoxication inhibitors in several major O,O-dimethyl phosphorodithioate insecticides. Our recent studies show extensive S-methylation of mono- and dithiocarbamic acids in mice, suggesting the possibility that phosphorodithioic acids such as (MeO)2P(S)SH might also undergo S-methylation. This possibility was examined in ip-treated mice with emphasis on the metabolites of dimethoate [(MeO)2P(S)SCH2C(O)NHMe], one of the most important organophosphorus insecticides. The urinary metabolites of dimethoate, which contains no P-SMe substituent, were found to include four compounds with P-SMe moieties identified by 31P NMR spectroscopy as MeO(HS)P(O)SMe, MeO(HO)P(O)SMe, (MeO)2P(S)SMe, and (MeO)2P-(O)SMe; the latter two compounds are also established by GC-MS as dimethoate metabolites in mouse urine, liver, kidney, and lung. Several approaches verified unequivocally that the previously unknown P-SMe metabolites in urine and tissues are due to in vivo S-methylation rather than to impurities. Studies with other O,O-dimethyl and O,O-diethyl phosphorodithioate insecticides established the analogous S-methylation pathway for ethion, malathion, phenthoate, phosalone, and phosmet in mice. Thus, metabolism of O,O-dialkyl phosphorodithioate insecticides in mammals is shown here for the first time to yield S-methyl phosphorodithioates and phosphorothiolates from in vivo S- methylation of the intermediate O,O-dialkyl phosphorodithioic acids.