Demeton-S

Base Information

• Chemical Name: Demeton-S
• CAS No.: 126-75-0
• Molecular Formula: C8H19 O3 P S2
• Molecular Weight: 258.343
• European Community (EC) Number: 204-801-8
• ICSC Number: 0864
• UN Number: 3018
• UNII: 3UQ7N6O63K
• DSSTox Substance ID: DTXSID9037535
• Nikkaji Number: J5.387B
• Wikidata: Q2788153
• ChEMBL ID: CHEMBL1900921
• Mol file: 126-75-0.mol

Synonyms:Demeton-S;126-75-0;Thioldemeton;demeton s;Demetonthiol;ISOSYSTOX;Isodemeton;Izosystox;Thiol systox;PO-Systox;Demeton-S [ISO];Izosystox [Czech];Mercaptofos teolovy;IS [Pesticide];Diethyl S-(2-ethioethyl)thiophosphate;Mercaptofos teolovy [Russian];1-diethoxyphosphorylsulfanyl-2-ethylsulfanylethane;CHEBI:82117;HSDB 6201;EINECS 204-801-8;O,O-Diethyl S-(2-eththioethyl)phosphorothioate;BRN 1709166;UNII-3UQ7N6O63K;O,O-Diethyl S-ethyl-2-ethylmercaptophosphorothiolate;O,O-Dietyl-S-2-etylmerkaptoetyltiofosfat;O,O-Diethyl S-(2-(ethylthio)ethyl) phosphorothiolate;AI3-24045;3UQ7N6O63K;DTXSID9037535;O,O-Dietil-S-(2-etiltio-etil)-monotiofosfato;Phosphorothioic acid, O,O-diethyl S-(2-(ethylthio)ethyl) ester;Phosphorothioic acid, O,O-diethyl S-[2-(ethylthio)ethyl] ester;IS (pesticide);O,O-Diethyl S-2-(ethylthio)ethyl phosphorothioate;O,O-Dietyl-S-2-etylmerkaptoetyltiofosfat [Czech];O,O-Diethyl-S-(2-ethylthio-ethyl)-monothiofosfaat;O,O-Diaethyl-S(2-aethylthio-aethyl)-monothiophosphat;IS;O,O-Dietil-S-(2-etiltio-etil)-monotiofosfato [Italian];O,O-Diethyl-S-(2-ethylthio-ethyl)-monothiofosfaat [Dutch];Thiophosphate de O,O-diethyle et de S-(2-ethylthio-ethyle);O,O-Diaethyl-S(2-aethylthio-aethyl)-monothiophosphat [German];Ethanethiol, 2-(ethylthio)-, S-ester with O,O-diethyl phosphorothioate;Thiophosphate de O,O-diethyle et de S-(2-ethylthio-ethyle) [French];O,O-Diethyl S-[2-(ethylthio)ethyl] thiophosphate;diethyl {[2-(ethylsulfanyl)ethyl]sulfanyl}phosphonate;Systox-thiol;O,O-diethyl S-(2-(ethylthio)ethyl) phosphorothioate;O,O-Diethyl S-[2-(Ethylthio)ethyl] phosphorothioate;Disulfoton oxon;Demeton thiolo;C8H19O3PS2;Ethylthionodemeton;DEMETONS;DEMETON-S [MI];DEMETON-S [HSDB];DSSTox_CID_2306;DSSTox_RID_76540;DSSTox_GSID_22306;SCHEMBL117918;O,O-Diethyl S-[2-(Ethylthio)ethyl]phosphorothioate;DTXCID202306;CHEMBL1900921;BCP07259;Tox21_200239;Tox21_303989;BDBM50487988;Demeton-S 10 microg/mL in Isooctane;AKOS015898642;Demeton-S 1000 microg/mL in Acetone;NCGC00163826-01;NCGC00257793-01;NCGC00357287-01;CAS-126-75-0;CAS-8065-48-3;LS-108627;CS-0443894;Demeton-S 1000 microg/mL in Dichloromethane;C18978;O,O-diethyl S-[2-(ethylthio)ethyl]-thiophosphate;J-005432;Q2788153

Chemical Property of Demeton-S

Chemical Property:

• Appearance/Colour: COLOURLESS OILY LIQUID
• Vapor Pressure: 0.000595mmHg at 25°C
• Melting Point: 95-97℃
• Refractive Index: 1.5207 (589.3 nm 20℃)
• Boiling Point: 320.5 °C at 760 mmHg
• Flash Point: 147.6 °C
• PSA: 95.94000
• Density: 1.146 g/cm³
• LogP: 3.65380
• Storage Temp.: 0-6°C
• Water Solubility.: 2g/L(20 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 258.05132381
• Heavy Atom Count: 14
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Demeton-S ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 27/28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=O)(OCC)SCCSCC
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system. This may result in convulsions and respiratory depression. Cholinesterase inhibition. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
• Uses: Colinesterase inhibitor. Insecticide

Technology Process of Demeton-S

There total 15 articles about Demeton-S which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

1-bromo-2-(ethylsulphanyl)ethane (35420-95-2) + tetramethylammonium - O,O-diethyl phosphorothioate (30128-40-6) → Demeton-S (126-75-0)

Guidance literature:

In acetonitrile; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1002/adsc.201701549

Reference yield: 75.0%

2-ethylsulfanyl-ethanethiol (26750-44-7) + phosphonic acid diethyl ester (762-04-9) → Demeton-S (126-75-0)

Guidance literature:

With oxygen; caesium carbonate; In acetonitrile; at 30 ℃; for 3h; Schlenk technique;

DOI:10.1002/anie.201612190

Reference yield: 23.0%

phosphonic acid diethyl ester (762-04-9) + 2-Chloroethyl ethyl sulfide (693-07-2) → Demeton-S (126-75-0)

Guidance literature:

With sodium; sulfur; In toluene; at 60 ℃; for 144h; 1.) 25 deg C, 3 h; 2.) 90 deg C, 2 h;

DOI:10.1016/0040-4020(95)00413-3

upstream raw materials:

O,O-diethyl-S-(2-bromoethyl)thiophosphate

sodium thioethylate

demeton-O

1-ethylsulfanyl-2-thiocyanato-ethane

Downstream raw materials:

O,O-diethyl S-<2-(ethylsulfinyl)ethyl>phosphorothioate

O,O-diethyl S-<2-(ethylsulfonyl)ethyl>phosphorothioate

Diethyl phosphate

2-ethylsulfanyl-ethanethiol

Refernces

• 1、 Muller,Goldenson. "-". . p. 5182. Retrieved 1956.
• 2、 Gardner,Heath. "". . p. 1849,1851. Retrieved 1953.
• 3、 Kovács, Szabolcs,Bayarmagnai, Bilguun,Aillerie, Alexandre,Goo?en, Lukas J.. "Practical Reagents and Methods for Nucleophilic and Electrophilic Phosphorothiolations". supporting information. p. 1913 - 1918. Retrieved 2018/03/30.
• 4、 -. "A thiophosphate synthetic method of compound and the method in a plurality of pharmaceutical application in the synthesis of (by machine translation)". Paragraph 0239; 0240; 0241; 0242. . Retrieved 2017/07/20.