Acetoxon

Base Information

• Chemical Name: Acetoxon
• CAS No.: 2425-25-4
• Molecular Formula: C8H17 O5 P S
• Molecular Weight: 256.26
• UNII: J4K0KB7I7Y
• DSSTox Substance ID: DTXSID8041581
• Nikkaji Number: J7.888C
• Wikidata: Q27281190
• Mol file: 2425-25-4.mol

Synonyms:ACETOXON;Acetophos;Acetaphos;2425-25-4;Acetofos;Ethyl ((diethoxyphosphinyl)thio)acetate;ethyl 2-diethoxyphosphorylsulfanylacetate;HSDB 2030;UNII-J4K0KB7I7Y;BRN 1793591;J4K0KB7I7Y;AI3-27526;O,O-Diethyl S-carbethoxymethyl thiophosphate;O,O-Diethyl S-carboethoxymethyl thiophosphate;O,O-Diethyl S-carboethoxymethyl phosphorothioate;O,O-Diethyl S-(carbethoxy)methyl phosphorothiolate;Phosphorothioic acid, O,O-diethyl ester, S-ester with ethyl mercaptoacetate;Acetic acid, ((diethoxyphosphinyl)thio)-, ethyl ester;Acetic acid, mercapto-, ethyl ester, S-ester with O,O-diethyl phosphorothioate;Acetic acid, [(diethoxyphosphinyl)thio]-, ethyl ester;ACETOXON [HSDB];C8H17O5PS;SCHEMBL5933967;DTXSID8041581;Q27281190;PHOSPHOROTHIOIC ACID, O,O-DIETHYL S-CARBOETHOXYMETHYL ESTER

Chemical Property of Acetoxon

Chemical Property:

• Vapor Pressure: 0.00116mmHg at 25°C
• Boiling Point: 299.8°Cat760mmHg
• Flash Point: 135.1°C
• PSA: 96.94000
• Density: 1.192g/cm³
• LogP: 2.46380
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 256.05343181
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

99% ^*data from raw suppliers

ETHYL ((DIETHOXYPHOSPHINYL)THIO)ACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOC(=O)CSP(=O)(OCC)OCC

Technology Process of Acetoxon

There total 7 articles about Acetoxon 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: 63.0%

ethyl 2-sulfanylacetate (623-51-8) + phosphonic acid diethyl ester (762-04-9) → O,O-diethyl s-carboethoxymethyl phosphorothioate (2425-25-4)

Guidance literature:

With oxygen; caesium carbonate; In acetonitrile; at 30 ℃; for 12h; Schlenk technique;

DOI:10.1002/anie.201612190

Reference yield:

diethyl 2,2'-disulfanediyldiacetate (1665-65-2) + phosphonic acid diethyl ester (762-04-9) → O,O-diethyl s-carboethoxymethyl phosphorothioate (2425-25-4)

Guidance literature:

With tetraethylammonium perchlorate; sodium bromide; In acetonitrile;

DOI:10.1021/jo01330a025

Reference yield:

2,3,4,6,7,8,9,10‐octahydropyrimido[1,2‐a]azepin‐1‐ium O,O‐diethylphosphorothioate + ethyl bromoacetate (105-36-2) → O,O-diethyl s-carboethoxymethyl phosphorothioate (2425-25-4)

Guidance literature:

In acetonitrile; for 3h; Reflux;

DOI:10.1002/adsc.202000059

upstream raw materials:

diethyl phosphorochloridothioate

chloroacetic acid ethyl ester

Diethyl phosphonate

ethyl bromoacetate

Downstream raw materials:

(E)-3-cyclohexyl-acrylic acid ethyl ester

ethyl (2E)-oct-2-enoate

ethyl (Z)-oct-2-enoate

ethyl (E)-dodec-2-enoate

Refernces

• 1、 Jones, David J.,O'Leary, Eileen M.,O'Sullivan, Timothy P.. "A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates". supporting information. . Retrieved 2020/03/27.
• 2、 -. "A thiophosphate synthetic method of compound and the method in a plurality of pharmaceutical application in the synthesis of (by machine translation)". Paragraph 0135; 0136; 0137; 0138. . Retrieved 2017/07/20.