Nitrofen

Base Information

• Chemical Name: Nitrofen
• CAS No.: 1836-75-5
• Deprecated CAS: 51274-07-8
• Molecular Formula: C12H7Cl2NO3
• Molecular Weight: 284.098
• Hs Code.: 29093090
• European Community (EC) Number: 217-406-0
• ICSC Number: 0929
• UN Number: 3077
• UNII: N71UYG034A
• DSSTox Substance ID: DTXSID7020970
• Nikkaji Number: J31.991K
• Wikipedia: Nitrofen
• Wikidata: Q414023
• NCI Thesaurus Code: C44411
• Metabolomics Workbench ID: 49656
• ChEMBL ID: CHEMBL561004
• Mol file: 1836-75-5.mol

Synonyms:1,3-dichlorophenyl-p-nitrophenyl ether;2,4-dichloro-1-(4-nitrophenoxy)benzene;2,4-dichlorophenyl-4-nitrophenyl ether;nitrafen;nitrochlor;nitrofen

Chemical Property of Nitrofen

Chemical Property:

• Appearance/Colour: Colorless crystals or black solid
• Vapor Pressure: 4.55E-05mmHg at 25°C
• Melting Point: 69-70°C
• Refractive Index: 1.623
• Boiling Point: 360.6 °C at 760 mmHg
• Flash Point: 171.9 °C
• PSA: 55.05000
• Density: 1.451 g/cm³
• LogP: 5.21710
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Water Solubility.: 1mg/L(22 oC)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 282.9802985
• Heavy Atom Count: 18
• Complexity: 290
• Transport DOT Label: Class 9

Purity/Quality:

99.9% ^*data from raw suppliers

2,4-Dichloro-1-(4-nitrophenoxy)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 45-61-50/53-22
• Safety Statements: 45-53-61-60-50/53-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Protox-Inhibiting
• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2=C(C=C(C=C2)Cl)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the skin and respiratory tract. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes malformations in human babies.
• Uses: Formerly as herbicide.

Technology Process of Nitrofen

There total 12 articles about Nitrofen 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: 100.0%

4-Fluoronitrobenzene (350-46-9,178603-76-4) + 2,4-dichlorophenol (120-83-2,40477-79-0) → nitrofen (1836-75-5)

Guidance literature:

With cesium fluoride/clinoptilolite; In dimethyl sulfoxide; at 110 ℃; for 0.15h;

DOI:10.1139/cjc-2015-0300

Reference yield: 92.0%

4-trimethylammonium nitrobenzene trifluoromethanesulfonate + 2,4-dichlorophenol (120-83-2,40477-79-0) → nitrofen (1836-75-5)

Guidance literature:

2,4-dichlorophenol; With potassium hexamethylsilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

4-trimethylammonium nitrobenzene trifluoromethanesulfonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 5h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201712618

Reference yield: 66.0%

4-chlorobenzonitrile (100-00-5) + 2,4-dichlorophenol (120-83-2,40477-79-0) → nitrofen (1836-75-5)

Guidance literature:

With potassium fluoride supported on Clinoptilolite; In dimethyl sulfoxide; at 115 - 120 ℃; for 9h;

DOI:10.1002/ejoc.201001447

upstream raw materials:

4-chlorobenzonitrile

2,4-dichlorophenol

copper

bifenox

Downstream raw materials:

4-oxo-4-((4-(2,4-dichlorophenoxy)phenyl)amino)butanoic acid

4-nitro-phenol

2,4-dichlorophenol

2,4-dichloro-4'-aminodiphenyl ether

Refernces

• 1、 -. "AGRICULTURAL CHEMICALS". Page/Page column 56; 95. . Retrieved 2019/08/08.
• 2、 Antipin, Roman L.,Beshnova, Daria A.,Petrov, Rostislav A.,Shiryaeva, Anna S.,Andreeva, Irina P.,Grigorenko, Vitaly G.,Rubtsova, Maya Yu.,Majouga, Alexander G.,Lamzin, Victor S.,Egorov, Alexey M.. "Synthesis, SAR and molecular docking study of novel non-β-lactam inhibitors of TEM type β-lactamase". supporting information. p. 1588 - 1592. Retrieved 2017/03/17.