2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate

Base Information

• Chemical Name: 2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate
• CAS No.: 13171-21-6
• Molecular Formula: C₁₀H₁₉ClNO₅P
• Molecular Weight: 299.691
• Hs Code.: 29241200
• DSSTox Substance ID: DTXSID7021156
• ChEMBL ID: CHEMBL3182713
• Mol file: 13171-21-6.mol

Synonyms:[3-chloro-4-(diethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate;Phosophamidon;2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate;Fosfamidon [Dutch];Caswell No. 661;Fosfamidone [Italian];Phosphamidon 85 WSC;Foszfamidon (Hungarian);Phosphamidon;(Famfos);CCRIS 516;Phosphamidon [ANSI:BSI:ISO];DTXSID7021156;CHEBI:38832;HSDB 1754;Alfamidon;C10-H19-Cl-N-O5-P;EINECS 236-116-5;EPA Pesticide Chemical Code 018201;AI3-25515;Dimethyl-(diethylamido-1-chlorocrotonyl)-phosphate;Dimethyl-(diethylamido-1- chlorocrotonyl)-phosphate;N,N-Diethyl 2-chloro-3-dimethylphosphate crotonamide;2-Chloro-2-diethylcarbamyl-1-methylvinyl-dimethyl phosphate;2-Chloro-N,N-diethyl-3-hydroxycrotonamide dimethyl phosphate;Dimethyl phosphate of 2-chloro-N,N-diethyl-3-hydroxycrotonamide;2-Chloro-N,N-diethyl-3-hydroxycrotonamide ester with dimethyl phosphate;CHEMBL3182713;(2-Chloor-3-diethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-fosfaat [Dutch];(2-Chlor-3-diaethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-phosphat [German];(2-Cloro-3-dietilamino-1-metil-3-oxo-prop-1-en-il)-dimetil-fosfato [Italian];Dimethyl phosphate ester with 2-chloro-N,N-diethyl-3-hydroxycrotonamide (8CI);O,O-Dimethyl-O-(1-methyl-2-chlor-2-N,N-diaethyl-carbamoyl)-vinyl-phosphat [German];Phosphate de dimethyle et de (2-chloro-2-diethylcarbamoyl-1-methyl-vinyle) [French];Phosphoric acid 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propen-1-yl dimethyl ester;phosphoric acid dimethyl ester, ester with 2-chloro-N,N-diethyl-3-hydroxycrotonamide;Phosphamidon 1000 microg/mL in Acetone;Phosphamidon 10 microg/mL in Cyclohexane;Phosphamidon 100 microg/mL in Cyclohexane;(E)-3-chloro-4-(diethylamino)-4-oxobut-2-en-2-yl dimethyl phosphate

Chemical Property of 2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate

Chemical Property:

• Vapor Pressure: 3E-05mmHg at 25°C
• Melting Point: -45oC
• Refractive Index: 1.4718 (589.3 nm 25℃)
• Boiling Point: 160~162
• PKA: -1.61±0.70(Predicted)
• Flash Point: 169.1oC
• PSA: 74.88000
• Density: 1.21
• LogP: 2.74260
• Storage Temp.: 2-8°C
• Water Solubility.: Totally miscible
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 299.0689374
• Heavy Atom Count: 18
• Complexity: 359

Purity/Quality:

Phosphamidon PESTANAL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion, inhalation, skin absorption; cholinesterase inhibitor; use may be restricted.
• Hazard Codes: T+,N
• Statements: 24-28-50/53-68
• Safety Statements: 23-36/37-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C(=C(C)OP(=O)(OC)OC)Cl
• Description: Types of phosphamidon formulations include soluble liquid, suspension concentrate and emulsifiable concentrate, ULV liquid, and 10% granules Phosphamidon is a pale yellow to colourless oily liquid with a faint odour. It is miscible with water and is soluble in aromatic hydrocarbons. Technical phosphamidon is a pale yellow to colourless oily liquid with a faint odour. It consists of a mixture of (Z)-isomer and (E)-isomer in the approximate proportion of 70:30. It decomposes on heating and releases highly toxic fumes such as phosphorus oxides, hydrogen chloride, and nitrogen oxides. Phosphamidon reacts and gets rapidly hydrolysed by alkalis and decomposes on heating or on burning, producing highly toxic fumes. It attacks metals such as iron, tin, and aluminium. It is used as a broad-spectrum insecticide and acaricide for the control of pests and vectors on crops like sugarcane, rice, citrus orchards, and cotton.
• Uses: Insecticide used to control sap-feeding insects and other pests in a wide variety of crops Phosphamidon is used to control sucking and boring insects and mites in a very wide range of crops and in forestry applications. Insecticide.

Technology Process of 2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate

There total 3 articles about 2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate 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:

2,2-dichloro-acetoacetic acid diethylamide (16695-57-1) + phosphorous acid trimethyl ester (121-45-9) → dimecron (297-99-4,13171-21-6,23783-98-4)

Guidance literature:

With chlorobenzene;

Reference yield:

N,N-diethyl-3-oxobutanamide (2235-46-3) → dimecron (297-99-4,13171-21-6,23783-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SO₂Cl₂

2: chlorobenzene

With sulfuryl dichloride; In chlorobenzene;

DOI:10.1002/hlca.19610440621

Reference yield:

→ dimecron (297-99-4,13171-21-6,23783-98-4)

Guidance literature:

Trimethylphosphit, N,N-Diethyldichloracetoacetamid;

upstream raw materials:

2,2-dichloro-acetoacetic acid diethylamide

phosphorous acid trimethyl ester

N,N-diethyl-3-oxobutanamide