2327-02-8

Basic information

• Product Name: 1-(3,4-DICHLOROPHENYL)UREA
• Synonyms: (3,4-dichlorophenyl)-ure;1-(3,4-DICHLOROPHENYL)UREA;Urea, (3,4-dichlorophenyl)-;n'-3,4-dichlorophenylurea;3,4-DCPU;diuron-desdimethyl
• CAS NO: 2327-02-8
• Molecular Formula: C₇H₆Cl₂N₂O
• Molecular Weight: 205.04
• Mol File: 2327-02-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 155.6-156.3 °C
• Boiling Point: 302.2 °C at 760 mmHg
• Flash Point: 136.5 °C
• Appearance: /
• Density: 1.534
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• PKA: 13.45±0.70(Predicted)
• CAS DataBase Reference: 1-(3,4-DICHLOROPHENYL)UREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-DICHLOROPHENYL)UREA(2327-02-8)
• EPA Substance Registry System: 1-(3,4-DICHLOROPHENYL)UREA(2327-02-8)

Safety Data

• Hazardous Substances Data: 2327-02-8(Hazardous Substances Data)

Usage

Description

1-(3,4-Dichlorophenyl)urea, also known as Didemethyldiuron, is a chemical compound belonging to the class of ureas. It is characterized by the presence of a 3,4-dichlorophenyl group substituted at the 1-position of the urea molecule. 1-(3,4-DICHLOROPHENYL)UREA is a derivative of Diuron, a phenyl urea herbicide, and serves as a metabolite of the herbicide.

Uses

Used in Chemical Synthesis:
1-(3,4-Dichlorophenyl)urea is used as a reagent in the synthesis of hydatoin derivatives, which possess anticonvulsant properties. Its unique chemical structure allows it to participate in various chemical reactions, contributing to the development of new compounds with potential therapeutic applications.
Used in Agriculture:
In the agricultural industry, 1-(3,4-Dichlorophenyl)urea is used as a pre-emergent herbicide. Its application helps control the growth of unwanted plants, ensuring the healthy development of crops and increasing agricultural productivity.

InChI:InChI=1/C7H6Cl2N2O/c8-5-2-1-4(3-6(5)9)11-7(10)12/h1-3H,(H3,10,11,12)

Upstream product

• 102-36-3 3,4-dichlorophenylisocyanate 
• 132373-16-1 1-(3,4-Dichloro-phenyl)-3-[3,5,5-trimethyl-2-thioxo-thiazolidin-(4Z)-ylidene]-urea 
• 132373-08-1 1-(3,4-Dichloro-phenyl)-3-[3,4,4-trimethyl-2-thioxo-thiazolidin-(5Z)-ylidene]-urea 
• 116121-36-9 C₁₃H₁₅Cl₂N₃O₂S₂ 
• 116121-34-7 C₁₃H₁₅Cl₂N₃O₂S₂ 
• 132408-12-9 4-(3,4-Dichloro-phenyl)-2-(3,5,5-trimethyl-2-thioxo-thiazolidin-4-yl)-[1,2,4]oxadiazolidine-3,5-dione 
• 132373-06-9 4-(3,4-Dichloro-phenyl)-2-(3,4,4-trimethyl-2-thioxo-thiazolidin-5-yl)-[1,2,4]oxadiazolidine-3,5-dione 
• 95-50-1 1,2-dichloro-benzene 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 95-76-1 m,p-dichloroaniline 
• 917-61-3 sodium isocyanate 
• 401797-02-2 2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 99514-61-1 N-(5-chloro-2-hydroxy-phenyl)-N'-(3,4-dichloro-phenyl)-urea 
• 95428-71-0 N-<3,4-Dichlor-phenyl>-N'-<2-(cyclohexen-(1)-yl)-cyclohexen-(1)-yl>-harnstoff 
• 116121-40-5 1-(3,4-Dichloro-phenyl)-3-(3,5,5-trimethyl-2-oxo-thiazolidin-4-yl)-urea 
• 126381-35-9 1-(2-Cyano-acetyl)-3-(3,4-dichloro-phenyl)-urea 
• 330-54-1 DCMU 
• 116121-50-7 1-(3,4-Dichloro-phenyl)-3-(3,5,5-trimethyl-2-thioxo-thiazolidin-4-yl)-urea 
• 126381-38-2 6-Amino-1-(3,4-dichloro-phenyl)-1H-pyrimidine-2,4-dione 
• 126381-41-7 6-Amino-1-(3,4-dichloro-phenyl)-5-nitroso-1H-pyrimidine-2,4-dione 
• 126381-36-0 1-{2-Cyano-2-[(E)-hydroxyimino]-acetyl}-3-(3,4-dichloro-phenyl)-urea 
• 13142-49-9 1-(3,4-dichlorophenyl)-3-(pyridin-2-yl)urea 

Relevant articles and documents

Fungal biodegradation of a phenylurea herbicide, diuron: Structure and toxicity of metabolites

Microbial degradation, organic synthesis and ecotoxicology were used to investigate the fate of diuron after spreading on soils. Quantitative biodegradation assays were performed with fungal strains, showing that diuron was degraded but not entirely mineralized. The modifications observed consisted in demethylation of the terminal nitrogen atom. The identified metabolites were synthesized in sufficient amounts to confirm their structures and determine their non-target toxicity using four biotests. The two metabolites exhibited higher effects than parent diuron. This limited biodegradability and potential aquatic toxicity suggest that diuron is of higher environmental concern than previously recognized. (C) 2000 Society of Chemical Industry.

Disrupting the Conserved Salt Bridge in the Trimerization of Influenza A Nucleoprotein

Antiviral drug resistance in influenza infections has been a major threat to public health. To develop a broad-spectrum inhibitor of influenza to combat the problem of drug resistance, we previously identified the highly conserved E339?R416 salt bridge of the nucleoprotein trimer as a target and compound 1 as an inhibitor disrupting the salt bridge with an EC50 = 2.7 μM against influenza A (A/WSN/1933). We have further modified this compound via a structure-based approach and performed antiviral activity screening to identify compounds 29 and 30 with EC50 values of 110 and 120 nM, respectively, and without measurable host cell cytotoxicity. Compared to the clinically used neuraminidase inhibitors, these two compounds showed better activity profiles against drug-resistant influenza A strains, as well as influenza B, and improved survival of influenza-infected mice.

A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water

A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.