Methyl parathion

Base Information

• Chemical Name: Methyl parathion
• CAS No.: 298-00-0
• Deprecated CAS: 37359-35-6,63653-66-7,63653-66-7
• Molecular Formula: C8H10NO5PS
• Molecular Weight: 263.211
• Hs Code.: 29201100
• European Community (EC) Number: 206-050-1
• ICSC Number: 0626
• UN Number: 2783,3018
• UNII: 41BCL2O91D
• DSSTox Substance ID: DTXSID1020855
• Nikkaji Number: J2.981E
• Wikipedia: Parathion_methyl
• Wikidata: Q421693
• NCI Thesaurus Code: C163677
• Metabolomics Workbench ID: 55993
• ChEMBL ID: CHEMBL346516
• Mol file: 298-00-0.mol

Synonyms:Dalf;Metacid 50;Metaphos;Methyl Parathion;Methylparathion;Parathion Methyl;Vofatox;Wofatox

Chemical Property of Methyl parathion

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.25E-05mmHg at 25°C
• Melting Point: 36 °C
• Refractive Index: 1.556
• Boiling Point: 334.7 °C at 760 mmHg
• Flash Point: 156.2 °C
• PSA: 115.41000
• Density: 1.411 g/cm³
• LogP: 3.66470
• Storage Temp.: APPROX 4°C
• Water Solubility.: 0.005 g/100 mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 263.00173059
• Heavy Atom Count: 16
• Complexity: 279
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

97% ^*data from raw suppliers

Parathion-methyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, N, Xn, F
• Hazard Codes: T+;N,N,T+,Xn,F
• Statements: 5-24-26/28-48/22-50/53-10-67-66-51/53-36-20/22-11-65-38
• Safety Statements: 28-36/37-45-60-61-26-62-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: COP(=S)(OC)OC1=CC=C(C=C1)[N+](=O)[O-]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system. This may result in convulsions and respiratory depression. Cholinesterase inhibition. Exposure far above the OEL could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Description: Methyl parathion is an organophosphate insecticide. It is converted into an oxon-containing metabolite in vivo, similar to other organophosphate pesticides, that inhibits acetylcholinesterase. Methyl parathion is lethal to lab strains and field isolates of tobacco budworm larvae (LD50s = 7 and 81.8-128.3 μg/g, respectively). It reduces the number of stink bugs (C. sayi) caught per 100 net sweeps when applied to alfalfa fields at a concentration of 0.4 pounds per acre. Methyl parathion increases sister chromatid exchange (SCE) in a concentration-dependent manner and induces cell cycle arrest at the M1 phase in V79 cells at a concentration of 40 μg/ml. It is toxic to rats (LD50 = 14 mg/kg).
• Uses: Methyl parathion is an insecticide and acaricide used to control boll weevils and many biting or sucking insect pests of agricultural crops. It kills insects by contact, stomach and respiratory action. Methyl parathion is available in dust, emulsifiable concentrate, ULV liquid, microencapsules and wettable powder formulations. Methyl parathion is one of a class of insecticides referred to as organophosphates. These chemicals act by interfering with the activities of cholinesterase, an enzyme that is essential for the proper working of the nervous systems of humans, animals and insects. Parathion-methyl is an derivative of Parathion (P192220), an organophosphate insecticide used on cotton, rice and fruit trees.

Technology Process of Methyl parathion

There total 5 articles about Methyl parathion 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: 58.0%

dimethyl thiophosphite (5930-72-3) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → parathion-methyl (298-00-0)

Guidance literature:

With tert.-butylhydroperoxide; lithium iodide; In water; acetonitrile; at 20 ℃; for 0.25h;

DOI:10.1002/ejoc.201901362

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + dimethyl chlorothiophosphate (2524-03-0) → parathion-methyl (298-00-0)

Guidance literature:

With sodium carbonate; acetone;

DOI:10.1021/ja01162a028

Reference yield:

dimethyl chlorothiophosphate (2524-03-0) + 4-nitrophenol sodium salt (824-78-2) → parathion-methyl (298-00-0)

Guidance literature:

In ethanol; for 1h; Yield given; Heating;

DOI:10.1016/0040-4020(95)00413-3

upstream raw materials:

4-(4-nitrophenoxy)butanoic acid

sodium methylate

4-nitro-phenol

dimethyl chlorothiophosphate

Downstream raw materials:

thiophosphoric acid S-methyl ester-O-(4-nitro-phenyl ester); trimethyl sulfonium-salt

methyl paraoxon

thiophosphoric acid S-methyl ester-O,O'-bis-(4-nitro-phenyl ester)

thiophosphoric acid O,S-dimethyl ester-O'-(4-nitro-phenyl ester)

Refernces

• 1、 Anitha, Thippani,Ashalu, Kashamalla Chinna,Sandeep, Mummadi,Mohd, Aabid,Wencel-Delord, Joanna,Colobert, Francoise,Reddy, Kallu Rajender. "LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates". . p. 7463 - 7474. Retrieved 2019/12/03.
• 2、 Catrina, Irina E.,Hengge, Alvan C.. "Comparisons of phosphorothioate with phosphate transfer reactions for a monoester, diester, and triester: Isotope effect studies". . p. 7546 - 7552. Retrieved 2007/10/03.