Amiton

Base Information

• Chemical Name: Amiton
• CAS No.: 78-53-5
• Deprecated CAS: 102388-58-9
• Molecular Formula: C10H24 N O3 P S
• Molecular Weight: 269.345
• UN Number: 3018
• UNII: 7SD1SH009V
• DSSTox Substance ID: DTXSID6058184
• Nikkaji Number: J5.507G
• Wikipedia: VG_(nerve_agent)
• Wikidata: Q419110
• Mol file: 78-53-5.mol

Synonyms:amiton;amiton oxalate (1:1);O,O-diethyl S-(diethylaminoethyl) phosphorothiolate

Chemical Property of Amiton

Chemical Property:

• Melting Point: 25°C
• Refractive Index: nD27 1.4655
• Boiling Point: bp0.01 76°; bp0.2 110°
• PKA: 9.39±0.25(Predicted)
• Flash Point: 144.3oC
• PSA: 73.88000
• Density: 1.070±0.06 g/cm3(Predicted)
• LogP: 3.24250
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 269.12145180
• Heavy Atom Count: 16
• Complexity: 202
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Cholinesterase inhibitor. Use may be restricted.
• Hazard Codes: Cholinesterase inhibitor. Use may be restricted.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCN(CC)CCSP(=O)(OCC)OCC
• Uses: Insecticide.

Technology Process of Amiton

There total 13 articles about Amiton 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: 76.0%

Diethyl phosphonate (762-04-9,123-22-8) + diethylamino 2-diethylaminoethyl sulfide (137584-14-6) → O,O-diethyl S-(2-diethylaminoethyl) thiophosphate (78-53-5)

Guidance literature:

With zinc(II) chloride; In dichloromethane;

Reference yield: 7.0%

diethyl chlorophosphate (814-49-3) + 2-(diethylamine)ethanethiol (100-38-9) → O,O-diethyl S-(2-diethylaminoethyl) thiophosphate (78-53-5)

Guidance literature:

2-(diethylamine)ethanethiol; With n-butyllithium; In diethyl ether; hexane; at 20 ℃; Cooling with acetone-dry ice; Inert atmosphere;

diethyl chlorophosphate; In diethyl ether; hexane; at 20 ℃; for 3h; Cooling with acetone-dry ice; Inert atmosphere;

Reference yield:

2-(Diethylamino)ethanol (100-37-8) → O,O-diethyl S-(2-diethylaminoethyl) thiophosphate (78-53-5)

Guidance literature:

With sodium hydride; benzene; und anschliessend mit Thiophosphorsaeure-O,O'-diaethylester-chlorid;

DOI:10.1021/ja01579a063 DOI:10.1002/jsfa.2740090808

upstream raw materials:

O,O-diethyl S-[2(diethylamino)ethyl]phosphorothionothiolate

phosphonic acid diethyl ester

2-(Diethylamino)ethanol

diethyl chlorophosphate

Downstream raw materials:

2-(diethylamine)ethanethiol

Refernces

• 1、 Althoff, Marc A.,Grieger, Kathrin,H?rtel, Martin A. C.,Karaghiosoff, Konstantin L.,Klap?tke, Thomas M.,Metzulat, Manfred. "Application of the Transpiration Method to Determine the Vapor Pressure and Related Physico-Chemical Data of Low Volatile, Thermolabile, and Toxic Organo(thio)phosphates". . p. 2603 - 2609. Retrieved 2017/05/29.
• 2、 Bigley, Andrew N.,Mabanglo, Mark F.,Harvey, Steven P.,Raushel, Frank M.. "Variants of Phosphotriesterase for the Enhanced Detoxification of the Chemical Warfare Agent VR". . p. 5502 - 5512. Retrieved 2015/09/15.