140-38-5

Usage

Uses

Used in Agricultural Industry:
4-Chlorophenylurea is used as a plant growth regulator for its ability to control the growth and development of plants. It is particularly effective in inhibiting shoot growth and promoting the development of lateral buds, which can be beneficial for crop management and yield optimization.
Used in Research Studies:
In scientific research, 4-Chlorophenylurea is utilized to investigate its effects on photosynthetic processes. Understanding its impact on these processes can provide insights into plant physiology and potentially lead to the development of strategies for improving crop productivity.
Used in Plant Disease and Pest Management:
4-Chlorophenylurea is also used in studies focused on plant disease and pest control. Its potential role in managing these issues could contribute to the development of more effective and environmentally friendly pest management strategies.
Used in Postharvest Quality Improvement:
Lastly, 4-Chlorophenylurea is being explored for its potential to improve the shelf life and postharvest quality of fruits and vegetables. This application could have significant implications for the food industry by reducing spoilage and waste, and ensuring that produce remains fresh for longer periods.

InChI:InChI=1/C7H7ClN2O/c8-5-1-3-6(4-2-5)10-7(9)11/h1-4H,(H3,9,10,11)

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 60-29-7 diethyl ether 
• 45964-97-4 1-(4-chlorophenyl)guanidine 
• 64-10-8 phenyl carbamate 
• 113546-44-4 N-chloro-N'-phenyl-urea 
• 684-93-5 1-methyl-1-nitrosourea 
• 106-47-8 4-chloro-aniline 
• 590-28-3 potassium cyanate 
• 57-13-6 urea 
• 103-72-0 phenyl isothiocyanate 
• 2386-64-3 ethylmagnesium chloride 
• 100-66-3 methoxybenzene 
• 1219-99-4 N,N'-bis(4-chlorophenyl)urea 
• 110-89-4 piperidine 

Downstream Products

• 859732-53-9 1-(4-chloro-6-methyl-2-pyrimidinyl)-3-(p-chlorophenyl)urea 
• 102395-63-1 1-(4-chloro-phenylcarbamoyl)-4-phenyl-piperidine-4-carboxylic acid ethyl ester 
• 1219-99-4 N,N'-bis(4-chlorophenyl)urea 
• 2621-80-9 ethyl p-chlorophenylcarbamate 
• 32772-86-4 N-acetyl-N'-(4-chloro-phenyl)-urea 
• 148719-19-1 N-<(4-methylphenyl)sulfinyl>-N'-(4-chlorophenyl)urea 
• 58247-24-8 1-(4-chlorophenyl)-3-amidinourea 
• 65440-23-5 4-(4-chloro-phenyl)-allophanic acid ethyl ester 
• 872265-87-7 N-chloro-N'-(4-chloro-phenyl)-urea 
• 872265-82-2 N,N-dichloro-N'-(2,4-dichloro-phenyl)-urea 
• 872265-83-3 N-chloro-N'-(2,4,6-trichloro-phenyl)-urea 
• 100948-89-8 (4-chloro-2,6-dinitro-phenyl)-urea 
• 92104-42-2 1-(4-chloro-phenyl)-5-furfurylidene-imidazolidine-2,4-dione 
• 94378-57-1 N-<4-Chlor-phenyl>-N'-<2-(cyclohexen-(1)-yl)-cyclohexen-(1)-yl>-harnstoff 

Relevant academic research and scientific papers

Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents

A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.

Nano cerium oxide as a recyclable catalyst for the synthesis of N-monosubstituted ureas with the aid of acetaldoxime as an effective water surrogate

A new method for the synthesis of N-monosubstituted ureas has been developed by the reaction of cyanamides with acetaldoxime in the presence of nano cerium oxide as an efficient and recyclable catalyst.

Synthesis of Five-Membered Cyclic Guanidines via Cascade [3 + 2] Cycloaddition of α-Haloamides with Organo-cyanamides

The convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved through a cascade [3 + 2] cycloaddition between organo-cyanamides and α-haloamides under mild conditions in good to excellent yields (up to 99%). The corresponding cyclic guanidines could be easily transformed into hydantoins via hydrolysis.

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.

Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas

A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.

Catalytic hydration of cyanamides with phosphinous acid-based ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights

The synthesis of a large variety of ureas R1R2NC(O)NH2 (R1 and R2 = alkyl, aryl or H; 26 examples) was successfully accomplished by hydration of the corresponding cyanamides R1R2NCN using the phosphinous acid-based complexes [MCl2(η6-p-cymene)(PMe2OH)] (M = Ru (1), Os (2)) as catalysts. The reactions proceeded cleanly under mild conditions (40-70 °C), in the absence of any additive, employing low metal loadings (1 molpercent) and water as the sole solvent. In almost all the cases, the osmium complex 2 featured a superior reactivity in comparison to that of its ruthenium counterpart 1. In addition, for both catalysts, the reaction rates observed for the hydration of the cyanamide substrates were remarkably faster than those involving classical aliphatic and aromatic nitriles. Computational studies allowed us to rationalize all these trends. Thus, the calculations indicated that the presence of a nitrogen atom directly linked to the CN bond depopulates electronically the nitrile carbon by inductive effect when coordinated to the metal center, thus favouring the intramolecular nucleophilic attack of the OH group of the phosphinous acid ligand to this carbon. On the other hand, the higher reactivity of Os vs. Ru seems to be related with the lower ring strain on the incipient metallacycle that starts to form in the transition state associated with this key step in the catalytic cycle. Indirect experimental evidence of the generation of the metallacyclic intermediates was obtained by studying the reactivity of [RuCl2(η6-p-cymene)(PMe2OH)] (1) towards dimethylcyanamide in methanol and ethanol. The reactions afforded compounds [RuCl(η6-p-cymene)(PMe2OR)(NCNMe2)][SbF6] (R = Me (5a), Et (5b)), resulting from the alcoholysis of the metallacycle, which could be characterized by single-crystal X-ray diffraction. This journal is

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.

Efficient Direct Halogenation of Unsymmetrical N -Benzyl- and N -Phenylureas with Trihaloisocyanuric Acids

A simple and efficient methodology for the direct halogenation of N -phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N -phenylureas with different patterns of substitution. Additionally, less reactive N -benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas

Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.