O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate

Base Information

• Chemical Name: O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate
• CAS No.: 2104-64-5
• Molecular Formula: C14H14 N O4 P S
• Molecular Weight: 323.309
• Hs Code.: 2930909090
• European Community (EC) Number: 218-276-8
• ICSC Number: 0753
• NSC Number: 404840,8943
• UN Number: 3018,2783
• UNII: 9Y6HP0HYA8
• DSSTox Substance ID: DTXSID7022174
• Nikkaji Number: J2.140G
• Wikipedia: EPN_(insecticide)
• Wikidata: Q2007270
• Metabolomics Workbench ID: 55025
• ChEMBL ID: CHEMBL3184641
• Mol file: 2104-64-5.mol

Synonyms:ENT 17,798;ENT-17,798;ENT17,798;EPN 300;EPN-300;EPN300;O-Ethyl-O-(4-nitrophenyl)phenylphosphonothioate;Phenylphosphonothioic Acid, 2-Ethyl 2-(4-Nitrophenyl) Ester

Chemical Property of O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate

Chemical Property:

• Appearance/Colour: acetonitrile.">often supplied as a solution in acetonitrile.
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Melting Point: 36 C
• Refractive Index: 1.6021 (589.3 nm 25℃)
• Boiling Point: 434.5°Cat760mmHg
• Flash Point: 216.6°C
• PSA: 106.18000
• Density: 1.34g/cm³
• LogP: 4.81890
• Storage Temp.: APPROX 4°C
• Solubility.: Miscible with acetone, benzene, methanol, isopropanol, toluene, and xylene (Windholz et al., 1983)
• Water Solubility.: 6.6 mg l-1 (20 °C, est.)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 323.03811610
• Heavy Atom Count: 21
• Complexity: 387
• Transport DOT Label: Poison

Purity/Quality:

EPN ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A cholinesterase inhibitor, absorbed by skin, use may be restricted. TLV: 0.1 mg/m³ (skin); not classifiable as a human carcinogen.
• Hazard Codes: T+,N,Xn,F
• Statements: 27/28-50/53-36-20/21/22-11
• Safety Statements: 22-36/37-45-60-61-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=S)(C1=CC=CC=C1)OC2=CC=C(C=C2)[N+](=O)[O-]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. Cholinesterase inhibition. The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. 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.
• Physical properties: Yellow to brown crystalline powder with an aromatic-like odor.
• Uses: EPN is used to control chewing insects, especially lepidopterous larvae in cotton, rice, fruit and vegetables. Insecticide; acaricide. Acaricide; insecticide

Technology Process of O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate

There total 7 articles about O-Ethyl O-(4-nitrophenyl) phenylphosphonothioate 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: 32.4%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + O,O-diethyl phosphoric O-ethyl phenylphosphonothioic anhydride (221616-24-6) → EPN (2104-64-5)

Guidance literature:

With potassium carbonate; In acetone; for 1.16667h; Heating;

DOI:10.1271/bbb.63.424

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → EPN (2104-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 40percent aq. NaOH / benzyltriethylammonium chloride / benzene / 0.75 h / Ambient temperature

2: K₂CO₃ / benzyltriethylammonium chloride / benzene / 3 h / Heating

With sodium hydroxide; potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride; In benzene;

Reference yield:

phenylthiophosphonic acid dichloride (3497-00-5) → EPN (2104-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 40percent aq. NaOH / benzyltriethylammonium chloride / benzene / 0.75 h / Ambient temperature

2: K₂CO₃ / benzyltriethylammonium chloride / benzene / 3 h / Heating

With sodium hydroxide; potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride; In benzene;

upstream raw materials:

4-(4-nitrophenoxy)butanoic acid

O-ethyl phenylphosphonochloridothioate

ethanol

O,O-Bis<4-nitrophenyl> benzenephosphonothioate

Downstream raw materials:

diethyl phenylphosphonothioate

EPN oxon

Refernces

• 1、 Yoshikawa, Hiromichi. "New synthesis of optically active O-aryl O-ethyl phenylphosphonothionates". . p. 424 - 426. Retrieved 2007/10/03.
• 2、 -. "Pyrazole oxime derivatives and compositions". . . Retrieved 2008/06/13.