Chlorfenvinfos

Base Information

• Chemical Name: Chlorfenvinfos
• CAS No.: 470-90-6
• Molecular Formula: C12H14Cl3O4P
• Molecular Weight: 359.574
• Hs Code.: 29199000
• European Community (EC) Number: 207-432-0
• ICSC Number: 1305
• UN Number: 3018
• UNII: WO4EMF0QD6
• Nikkaji Number: J657B
• Wikipedia: Chlorfenvinphos
• Wikidata: Q98966972
• Metabolomics Workbench ID: 55930
• ChEMBL ID: CHEMBL1411951
• Mol file: 470-90-6.mol

Synonyms:Benzylalcohol, 2,4-dichloro-a-(chloromethylene)-, diethyl phosphate (6CI);Phosphoric acid,2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl ester (8CI);2,4-Dichloro-a-(chloromethylene)benzyldiethylphosphate;2-Chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate;Birlan;Birlane;Birlane 10G;CVP;CVP (pesticide);Chlorfenvinfos;Chlorfenvinphos;Chlorphenvinfos;Chlorphenvinphos;Clofenvinfos;Compound 4072;Defiance S;Dermaton;Diethyl 1-(2,4-dichlorophenyl)-2-chlorovinyl phosphate;Diethyl2-chloro-1-(2,4-dichlorophenyl)vinyl phosphate;ENT 24969;Enolofos;GC 4072;Haptasol;O,O-Diethyl O-[1-(2,4-dichlorophenyl)-2-chlorovinyl] phosphate;O,O-Diethyl O-[2-chloro-1-(2,4-dichlorophenyl)vinyl] phosphate;OMS 1328;Quirlan;SD 7859;Sapecron;Sapecron 50EC;Supona;Tarene;Unitox;Vinyphate;Zaprawa enolofos;

Chemical Property of Chlorfenvinfos

Chemical Property:

• Appearance/Colour: Amber-colored liquid with a mild chemical odor
• Vapor Pressure: 3.9E-06mmHg at 25°C
• Melting Point: -23 to -19oC
• Refractive Index: 1.534
• Boiling Point: 396.5 °C at 760 mmHg
• Flash Point: 298.9 °C
• PSA: 54.57000
• Density: 1.373 g/cm³
• LogP: 5.72830
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 357.969529
• Heavy Atom Count: 20
• Complexity: 368
• Transport DOT Label: Poison

Purity/Quality:

Chlorfenvinphos ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+N
• Hazard Codes: T+;N,N,T+,Xn,F
• Statements: 24-28-50/53-67-65-38-11-26-20
• Safety Statements: 28-36/37-45-60-61-62-33-25-16-9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=O)(OCC)OC(=CCl)C1=C(C=C(C=C1)Cl)Cl
• Isomeric SMILES: CCOP(=O)(OCC)O/C(=C/Cl)/C1=C(C=C(C=C1)Cl)Cl
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Cholinesterase inhibition. Exposure could cause unconsciousness and death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Uses: Insecticide; acaricide. Chlorfenvinphos is used to control soil insects such as root worms on vegetables, bulb flies in wheat and maize and phorid and sciarid flies in mushrooms. It is also used to control Colorado beetles on potatoes, scale insects and mite eggs in citrus and stern borers and hoppers on rice. Other uses are the control of mosquitoes and animal ectoparasites as a sheep and cattle dip. From 1963 until the early 1990s, chlorfenvinphos was extensively used in veterinary products (dip, dust, and collars) for flea and tick control on pets and domestic animals, and in dairy barns, milk rooms, poultry houses, and other animal buildings. Agriculturally, it was used on potatoes, rice, and maize, and for control of soil insects and nematodes. All uses were canceled in the United States in 1991 and phased out in EU in 2006. Chlorfenvinphos continues to be used in Australia and New Zealand in veterinary products for combating ectoparasites on cattle and sheep.

Technology Process of Chlorfenvinfos

There total 6 articles about Chlorfenvinfos 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:

2,4-dichlorobenzoyl chloride (89-75-8) → Apachlor (470-90-6,18708-86-6,18708-87-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Zn(Cu) couple, 2.) Pd(PPh₃)4 / 1.) DMF, benzene, room temp., 1 h, then 60 deg C, 4 h, 2.) DMF, benzene, room temp., 1 h

2: 80 percent / benzyltrimethylammonium tetrachloroiodate / acetic acid / 2.5 h / 70 °C

3: diethyl ether / 1.5 h / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc copper; benzyltrimethylazanium tetrachloro-λ³-iodanuide; In diethyl ether; acetic acid;

DOI:10.1002/(SICI)1099-1344(199804)41:4<261::AID-JLCR77>3.0.CO;2-5

Reference yield:

1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → Apachlor (470-90-6,18708-86-6,18708-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / benzyltrimethylammonium tetrachloroiodate / acetic acid / 2.5 h / 70 °C

2: diethyl ether / 1.5 h / Ambient temperature

With benzyltrimethylazanium tetrachloro-λ³-iodanuide; In diethyl ether; acetic acid;

DOI:10.1002/(SICI)1099-1344(199804)41:4<261::AID-JLCR77>3.0.CO;2-5

Reference yield:

2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one (2274-66-0) + triethyl phosphite (122-52-1) → Apachlor (470-90-6,18708-86-6,18708-87-7) + 2-chloro-1-(2,4-dichlorophenyl)-ethenyl diethyl phosphate (18708-86-6)

Guidance literature:

In diethyl ether; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199804)41:4<261::AID-JLCR77>3.0.CO;2-5

upstream raw materials:

2,2-dichloro-1-(2,4-dichlorophenyl)ethan-1-one

[2-(2,6-Dichloro-phenyl)-2-oxo-ethyl]-phosphonic acid diethyl ester

triethyl phosphite

2,4-dichlorobenzoyl chloride

Refernces

• 1、 Mlotkowska, Barbara,Majewski, Piotr,Koziara, Anna,Zwierzak, Andrzej,Sledzinski, Bohdan. "REACTIONS OF 2,4- AND 2,6-DICHLOROPHENACYLIDENE HALIDES WITH TRIALKYLPHOSPHITES IN PROTIC SOLVENTS. DIRECT EVIDENCE FOR THE "ENOLATE ANION" PATHWAY". . p. 631 - 642. Retrieved 2007/10/02.