O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate

Base Information

• Chemical Name: O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate
• CAS No.: 3147-20-4
• Molecular Formula: C8H20 N O3 P S
• Molecular Weight: 241.291
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID10953477
• Nikkaji Number: J50.461K
• Wikidata: Q82932354
• ChEMBL ID: CHEMBL3277096
• Mol file: 3147-20-4.mol

Synonyms:217AO;O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate;O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate, oxalate (1:1);O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate, oxalate (2:1)

Chemical Property of O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate

Chemical Property:

• Vapor Pressure: 0.00375mmHg at 25°C
• Boiling Point: 280.6°Cat760mmHg
• PKA: 8.43±0.28(Predicted)
• Flash Point: 123.5°C
• PSA: 73.88000
• Density: g/cm³
• LogP: 2.46230
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 241.09015167
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

THIOPHOSPHORIC ACID O,O'-DIETHYL ESTER-S-(2-DIMETHYLAMINO-ETHYL ESTER) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(OCC)SCCN(C)C

Technology Process of O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate

There total 9 articles about O,O-diethyl S-(2-dimethylaminoethyl) phosphorothioate 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: 75.0%

Diethyl phosphonate (762-04-9,123-22-8) + C4H10ClNS*ClH → (S)-(2-(dimethylamino)ethyl) O,O-diethylphosphorothioate (3147-20-4)

Guidance literature:

With triethylamine; In dichloromethane; at -15 - 20 ℃; for 1h;

Reference yield: 69.0%

captamine (108-02-1) + phosphonic acid diethyl ester (762-04-9) → (S)-(2-(dimethylamino)ethyl) O,O-diethylphosphorothioate (3147-20-4)

Guidance literature:

With oxygen; nickel diacetate; yttrium(III) trifluoromethanesulfonate; In N,N-dimethyl-formamide; at 70 ℃; for 16h; Reagent/catalyst;

DOI:10.1021/acs.joc.9b00194

Reference yield:

2-(N,N-dimethylamino)ethylthiol hydrochloride (13242-44-9) + diethyl chlorophosphate (814-49-3) → (S)-(2-(dimethylamino)ethyl) O,O-diethylphosphorothioate (3147-20-4)

Guidance literature:

2-(N,N-dimethylamino)ethylthiol hydrochloride; With sodium; In methanol; at 25 - 65 ℃; for 1h; Green chemistry;

diethyl chlorophosphate; In toluene; at 0 - 40 ℃; Green chemistry;

upstream raw materials:

2-(N,N-dimethylamino)ethanol

O,O-diethyl O-[2-(dimethylamino)ethyl]phosphorothionate

captamine

diethyl chlorophosphate

Downstream raw materials:

echothiophate iodide

Refernces

• 1、 Song, Song,Zhang, Yiqun,Yeerlan, Adeli,Zhu, Bencong,Liu, Jianzhong,Jiao, Ning. "Cs2CO3-Catalyzed Aerobic Oxidative Cross-Dehydrogenative Coupling of Thiols with Phosphonates and Arenes". supporting information. p. 2487 - 2491. Retrieved 2017/02/23.
• 2、 -. "Echothiophate Iodide Process". Paragraph 0060; 0062-0063. . Retrieved 2017/01/23.