27205-99-8

Basic information

• Product Name: sodium O,O-diisopropyl dithiophosphate
• Synonyms: sodium O,O-diisopropyl dithiophosphate;Phosphorodithioic acid, O,O-bis(1-methylethyl) ester, sodium salt;Natrium-O,O-diisopropyldithiophosphat;phosphorodithioic acid, o,o-diisopropyl ester, sodium salt;Sodium diisopropyl phosphorodithioate;sodium diisopropyldithiophosphate;Dithiophosphoric acid O,O-diisopropyl ester sodium salt;Phosphorodithioic acid=O,O-bis(1-methylethyl)=S-sodium salt
• CAS NO: 27205-99-8
• Molecular Formula: C₆H₁₄NaO₂PS₂
• Molecular Weight: 236.267691
• EINECS: 248-322-2
• Product Categories: Dithiophosphate
• Mol File: 27205-99-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 189 °C
• Boiling Point: 257.1°Cat760mmHg
• Flash Point: 109.3°C
• Appearance: /
• Density: 1.145g/cm³
• PKA: 7.69[at 20 ℃]
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: sodium O,O-diisopropyl dithiophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium O,O-diisopropyl dithiophosphate(27205-99-8)
• EPA Substance Registry System: sodium O,O-diisopropyl dithiophosphate(27205-99-8)

Safety Data

• Hazardous Substances Data: 27205-99-8(Hazardous Substances Data)

Usage

Description

Sodium O,O-diisopropyl dithiophosphate is an organophosphate compound that serves as an intermediate in the synthesis of various chemicals, including Bensulide, an acetylcholinesterase inhibitor. It is characterized by its ability to inhibit acetylcholinesterase, which is a key enzyme in the nervous system.

Uses

Used in Pesticide Industry:
Sodium O,O-diisopropyl dithiophosphate is used as an intermediate for the synthesis of Bensulide (B166000), an organophosphate acetylcholinesterase inhibitor. sodium O,O-diisopropyl dithiophosphate is utilized as an herbicide for the protection of crops through pesticides, ensuring their healthy growth and increased yield.
Used in Environmental and Food Contaminant Monitoring:
Sodium O,O-diisopropyl dithiophosphate is also recognized as a Drinking Water Contaminant Candidate List 3 (CCL 3) compound by the United States Environmental Protection Agency (EPA). It is considered an environmental and food contaminant, and its presence is monitored to ensure the safety and quality of drinking water and the food supply.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H15O2PS2.Na/c1-5(2)7-9(10,11)8-6(3)4;/h5-6H,1-4H3,(H,10,11);/q;+1/p-1

Upstream product

• 84913-97-3 antimony tris(O,O-diisopropyl phosphorodithioate) 
• 67-63-0 isopropyl alcohol 
• 3031-21-8 bis(O,O-diisopropoxyphosphinothioyl)disulfide 
• 123381-62-4 N-methyl-4-chlorobenzohydroxamic acid sodium salt 

Downstream Products

• 65274-99-9 C₁₈H₃₃O₄P₃S₄ 
• 65275-02-7 C₁₈H₂₄O₂P₂S₂ 
• 69674-00-6 diisopropoxythiophosphoryl isothiocyanate 
• 7464-03-1 1,2-dithio-μ-trisulfido-diphosphoric acid tetra-O-isopropyl ester 
• 3031-21-8 bis(O,O-diisopropoxyphosphinothioyl)disulfide 
• 126443-52-5 diphenylantimony(III) O,O-((CH₃)2CH)2-dithiophosphate 
• 93441-33-9 Gd{(C₃H₇O)2PS₂}3{2C₆H₅CONH₂} 

Relevant articles and documents

On the reaction of bis(phosphothioyl)disulfanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

Among sodium N-alkyl-4-chlorobenzohydroxamates treated with bis(phosphothioyl)disulfanes >P(S)SSP(S)P(S) is phosphorothioyl, phosphonothioyl, and phosphinothioyl), only the N-methyl one yields quantitatively the respective O-phosphothioyl derivatives exhibiting complete inversion of configuration at phosphorus in a reaction whose products are inert toward dithiophosphate arising in the reaction. For branched N-alkyl benzohydroxamates, products of a SET process predominated. The mechanism of the title reaction is discussed.

NUCLEOPHILIC SUBSTITUTION REACTIONS ON ANTIMONY(III) 0,0-DISUBSTITUTED PHOSPHORODITHIOATES

Antimony(III) tris(O,O-diisobutyl phosphorodithioate), 1 (R=i-Bu) has been found to undergo a nucleophilic displacement reaction with sodium 1-propanethiolate to give antimony(III) tris-(1-propanethiolate), 4, and sodium O,O-diisobutyl phosphorodithioate (8, R=i-Bu).Reaction of 1 (R=i-Bu) with phenyllithium gave triphenylstibine and lithium O,O-diisobutyl phosphorodithioate.Similar reactions of various compounds of type 1 with the sodium salts of carboxylic acids and with the sodium salt of pyrrole were also found to occur.Furthermore, antimony tris(O,O-diisobutyl phosphorodithioate), 1 (R=i-Bu), was found to undergo solvolysis with n- propyl mercaptan to give 4 and O,O-diisobutyl phosphorodithioic acid 5.Compounds of type 1 are used as passivating agents in petroleum refining, and reactions of the types described for 1 with n-propyl mercaptan and with the salts of carboxylic acids probably occur when "Phil-Ad CA" is added to the feedstock of a fluid catalytic cracking unit.