Fenitrothion

Base Information

• Chemical Name: Fenitrothion
• CAS No.: 122-14-5
• Deprecated CAS: 12764-87-3,54182-70-6,94650-98-3,54182-70-6,94650-98-3
• Molecular Formula: C9H12NO5PS
• Molecular Weight: 277.238
• Hs Code.: 29201900
• European Community (EC) Number: 204-524-2
• ICSC Number: 0622
• UN Number: 3017,3018
• UNII: W8M4X3Y7ZY
• DSSTox Substance ID: DTXSID4032613
• Nikkaji Number: J2.492I
• Wikipedia: Fenitrothion
• Wikidata: Q417614
• NCI Thesaurus Code: C65655
• Metabolomics Workbench ID: 49608
• ChEMBL ID: CHEMBL347698
• Mol file: 122-14-5.mol

Synonyms:Phosphorothioicacid, O,O-dimethyl O-(4-nitro-m-tolyl) ester (6CI,8CI);Phosphorothioicacid, O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester;Accothion;Agria 1050;Agriya 1050;Agrothion;Arbogal;BAY 41831;Bayer 41831;Bayer S5660;CL 47300;CP 47114;Dimethyl 4-nitro-m-tolyl phosphorothionate;EI 47300;ENT 25,715;Fenition;

Chemical Property of Fenitrothion

Chemical Property:

• Appearance/Colour: brownish-yellow oil
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 3.4 °C
• Refractive Index: 1.552
• Boiling Point: 349.5 °C at 760 mmHg
• Flash Point: 165.2 °C
• PSA: 115.41000
• Density: 1.3227 g/cm³
• LogP: 3.97310
• Storage Temp.: APPROX 4°C
• Water Solubility.: 0.003 g/100 mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 277.01738065
• Heavy Atom Count: 17
• Complexity: 313
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

96% ^*data from raw suppliers

Fenitrothion ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn;N,N,Xn,T,F,T+
• Statements: 22-50/53-23-21/22-67-65-38-11-26
• Safety Statements: 2-60-61-45-36/37-62-28-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CC1=C(C=CC(=C1)OP(=S)(OC)OC)[N+](=O)[O-]
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the nervous system. This may result in convulsions, respiratory failure and death. Cholinesterase inhibition. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Description: Fenitrothion is a selective acaricide and contact insecticide of low ovicidal properties. It is a brown to yellow liquid with a characteristic odour. Fenitrothion belongs to the organophosphate family of insecticides. It acts by inhibiting cholinesterase, thus it is an effective pesticide against a wide range of pests such as chewing, penetrating, and sucking insect pests. These pests include locusts, coffee leaf miners, wheat bugs, rice stem borers, grain weevils, and grain beetles on orchard fruits, cereals, cotton, forests, and vegetables. Fenitrothion is also an effective household insecticide as well as vector control agent for malaria.
• Uses: Insecticide. Fenitrothion is used to control sucking, chewing and boring insects in cereals, soft fruit, tropical fruit, vines, sugar cane, vegetables, turf and forestry. It is also used as a public health insecticide for the control of flies, cockroaches and mosquitoes. Other uses are for the control of stored product pests and locusts.

Technology Process of Fenitrothion

There total 4 articles about Fenitrothion 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:

3-methyl-4-nitrophenol (2581-34-2,910311-23-8) + dimethyl chlorothiophosphate (2524-03-0) → MEP (122-14-5)

Guidance literature:

With triethylamine; In diethyl ether; at 35 ℃; for 5h;

DOI:10.5012/bkcs.2010.31.5.1339

Reference yield:

3-methyl-4-nitrophenol (2581-34-2,910311-23-8) → MEP (122-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH, 2.) thiophosphoryl trichloride / 2.) THF, reflux, 8 h

2: tetrahydrofuran / 2 h

With trichlorothiophosphine; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jf00039a044

Reference yield:

sodium methylate (124-41-4) + Thiophosphorochloridic acid O,O'-bis-(3-methyl-4-nitro-phenyl) ester → MEP (122-14-5) + O-methyl O,O-bis(3-methyl-4-nitro)phenyl phosphorothioate (4901-42-2)

Guidance literature:

In tetrahydrofuran; for 2h; Yield given. Yields of byproduct given;

DOI:10.1021/jf00039a044

upstream raw materials:

sodium methylate

3-methyl-4-nitrophenol

dimethyl chlorothiophosphate

Downstream raw materials:

O-ethyl-O,O-dimethylphosphorothioate

4-ethoxy-2-methyl-1-nitrobenzene

sodium 3-methyl-4-nitrophenolate

Natriumsalz des Thiophosphorsaeure-O,O-dimethylesters

Refernces

• 1、 -. "Oil-in-water emulsions". . . Retrieved 2008/06/13.
• 2、 -. "Oil-in-water emulsions". . . Retrieved 2008/06/13.